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Search for "benzyl alcohol" in Full Text gives 108 result(s) in Beilstein Journal of Organic Chemistry.

Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

  • Jiao-Na Han,
  • Cong Du,
  • Xinju Zhu,
  • Zheng-Long Wang,
  • Yue Zhu,
  • Zhao-Yang Chu,
  • Jun-Long Niu and
  • Mao-Ping Song

Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

Graphical Abstract
  • . Cyclopropylmethanol (2o), cyclohexylmethanol (2p), and adamantanemethanol (2q) were compatible with the transformation (45–56%). Moreover, an aliphatic ether and benzyl alcohol were proved to be effective coupling partners to provide 3ar and 3as in 68% and 70% yields, respectively. Compared with Co-catalyzed
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Published 09 Aug 2018

Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

  • Ugo Azzena,
  • Massimo Carraro,
  • Gloria Modugno,
  • Luisa Pisano and
  • Luigi Urtis

Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

Graphical Abstract
  • 4-(tetrahydro-2H-pyran-2-yloxymethyl)benzyl alcohol (4fb). Synthesis of 2-(2-phenylethoxy)tetrahydro-2H-pyran (3a). Supporting Information Supporting Information File 256: Full experimental details, copies of IR spectra of fresh and recycled NH4HSO4@SiO2 and copies of 1H and 13C NMR spectra.
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Published 03 Jul 2018

Mild and selective reduction of aldehydes utilising sodium dithionite under flow conditions

  • Nicole C. Neyt and
  • Darren L. Riley

Beilstein J. Org. Chem. 2018, 14, 1529–1536, doi:10.3762/bjoc.14.129

Graphical Abstract
  • coil mounted on a heating block and a back pressure regulator fitted at the output flow stream. Reagents were introduced through two 10 mL injection loops (Figure 2). Optimisation under flow conditions The flow reduction was initially optimised for the conversion of benzaldehyde to benzyl alcohol. The
  • coil reactor (Table 2, Figure 3). In order to better compare the flow and batch processes the reduction of benzaldehyde was repeated in a seal-tube vessel superheated to 110 °C with a reaction time of 64 min to match that of the optimised flow process. In this instance a 43% conversion to benzyl
  • alcohol was observed, indicating that under flow conditions, the simple superheating of the solvent was only partly responsible for the increased rate of reaction and that in all likelihood the improved mixing of the reagent streams also plays an important role. Further reduction of the residence time
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Published 22 Jun 2018

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

  • Akira Yoshimura,
  • Michael T. Shea,
  • Cody L. Makitalo,
  • Melissa E. Jarvi,
  • Gregory T. Rohde,
  • Akio Saito,
  • Mekhman S. Yusubov and
  • Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

Graphical Abstract
  • have investigated the analogous oxidatively assisted coupling reaction of carboxylic acids 9 with alcohols 10 or amine 12 using benziodazole 7a under similar conditions (Scheme 3). The reaction of butyric acid (9a) with benzyl alcohol (10a) using benziodiazole 7a in the presence of triphenylphosphine
  • and N,N-dimethyl-4-aminopyridine (DMAP) in chloroform solution under reflux conditions afforded the desired product 11a in good yield. As expected, the reactions of benzoic acid (9b) with benzyl alcohol (10a) or 1-pentanol (10b) under the same conditions gave the corresponding esters 11b or 11c in
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Published 08 May 2018

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

  • Eirinaios I. Vrettos,
  • Gábor Mező and
  • Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Graphical Abstract
  • ]. This type of linkers/spacers offers the capability to release the active drug after simultaneous cascade reactions, as shown in Figure 5. Para-amino benzyl alcohol (PABC; colored in red) is a representative example that can be connected in the amino group via an amide bond to an enzyme-hydrolyzable
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Published 26 Apr 2018

Volatiles from the xylarialean fungus Hypoxylon invadens

  • Jeroen S. Dickschat,
  • Tao Wang and
  • Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 734–746, doi:10.3762/bjoc.14.62

Graphical Abstract
  • index and best matching mass spectrum (Table 5). Notably, a common biosynthesis for all the identified aromatic compounds can be assumed that further strengthens their structure elucidations (Scheme 1). Starting from 11, an oxidation step at the 2-methyl group (red) could lead via the benzyl alcohol
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Published 29 Mar 2018

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

  • Morten M. C. H. van Schie,
  • Tiago Pedroso de Almeida,
  • Gabriele Laudadio,
  • Florian Tieves,
  • Elena Fernández-Fueyo,
  • Timothy Noël,
  • Isabel W. C. E. Arends and
  • Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

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  • Michaelis–Menten dependency of the enzyme activity (Figure 1). Apparent KM and kcat values of approximately 1 mM and 22 s−1 were estimated, respectively. These values are in the same order of magnitude as those for benzyl alcohol substrates reported previously [29]. The slightly decreasing enzyme activity
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Published 26 Mar 2018

Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of meso-cyclic anhydrides

  • Lingjun Xu,
  • Shuwen Han,
  • Linjie Yan,
  • Haifeng Wang,
  • Haihui Peng and
  • Fener Chen

Beilstein J. Org. Chem. 2018, 14, 309–317, doi:10.3762/bjoc.14.19

Graphical Abstract
  • different alcohols (Table 3). Excellent yields with high enantioselectivities were obtained in all cases. The sterically more bulky 2-propanol worked well in this reaction. Allylic alcohol, benzyl alcohol and cinnamyl alcohol were also well compatible in this bifunctional organocatalysis conditions to
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Published 31 Jan 2018

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

  • Neil S. Keddie,
  • Pier Alexandre Champagne,
  • Justine Desroches,
  • Jean-François Paquin and
  • David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

Graphical Abstract
  • reduced under Noyori’s conditions [12] using (S,S)-Ru(DPEN)2 as catalyst and [2H2]-formic acid as the deuterium source. This afforded the corresponding 7-[2H1]-(S)-benzyl alcohol ((S)-3) in moderate yield (81%) and high ee (95%), as evidenced by 2H-PBLG-NMR. Benzyl alcohol 3 was converted to the
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Published 09 Jan 2018

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

  • Mukta Shaw,
  • Yogesh Kumar,
  • Rima Thakur and
  • Amit Kumar

Beilstein J. Org. Chem. 2017, 13, 2385–2395, doi:10.3762/bjoc.13.236

Graphical Abstract
  • ), benzyl alcohol (2c), 4-methoxy benzyl alcohol (2d), and secondary alcohols, e.g., cyclohexanol (2e), cyclopentanol (2f) produced their corresponding glucosides 5b–f in 78–88% yields and with moderate α-selectivity (Table 2, entries 1–5). It is important to note that, when a halogenated primary alcohol
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Published 09 Nov 2017

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

  • Andrea Porcheddu,
  • Evelina Colacino,
  • Giancarlo Cravotto,
  • Francesco Delogu and
  • Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

Graphical Abstract
  • . Ideally, a dispersant should not interfere with the oxidation reaction, and should be inexpensive and eco-friendly, if possible. As a first choice, we dispersed benzyl alcohol (1b) on alumina and silica gel. However, the reaction did not go to completion. In contrast, it proceeded smoothly (10 min) and in
  • aromatic ring of the benzyl alcohol were also viable, giving the corresponding aromatic aldehydes in high yields regardless of the electronic nature of their substituents (aldehydes 2g–k in Scheme 3). Surprisingly, and contrary to Stahl’s original solution procedure [24], the oxidation of 2-hydroxybenzyl
  • was sealed and ball-milled for 1 min. Then, benzyl alcohol (216.3 mg, 207 μL, 2.0 mmol), NaCl (1.0 g) together with other two zirconia balls (12 mm Ø) were added and the reaction mixture was subjected to grinding for further 10 minutes overall (two cycles of 5 minutes each). The first milling cycle
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Published 02 Oct 2017

New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

  • Daily Rodríguez-Padrón,
  • Alina M. Balu,
  • Antonio A. Romero and
  • Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1982–1993, doi:10.3762/bjoc.13.194

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  • potential from an environmental point-of-view since it is able to reduce solvent issues in chemical syntheses. The catalytic activity of the obtained nanocatalysts was investigated in both the oxidation of benzyl alcohol to benzaldehyde and in the alkylation of toluene with benzyl chloride. The microwave
  • -assisted oxidation of benzyl alcohol reached 45% conversion after 10 min. The conversion of the alkylation of toluene in both microwave-assisted and conventional heating methods was higher than 99% after 3 min and 30 min, respectively. The transformation of benzyl alcohol and toluene into valuable product
  • in both the oxidation and alkylation reaction reveals a potential method for the valorization of lignocellulosic biomass. Keywords: alkylation; benzyl alcohol; benzyl chloride; iron oxide; mechanochemistry; microwave-assisted oxidation; polysaccharide; toluene; Introduction Heterogeneous catalysis
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Published 21 Sep 2017

Block copolymers from ionic liquids for the preparation of thin carbonaceous shells

  • Sadaf Hanif,
  • Bernd Oschmann,
  • Dmitri Spetter,
  • Muhammad Nawaz Tahir,
  • Wolfgang Tremel and
  • Rudolf Zentel

Beilstein J. Org. Chem. 2017, 13, 1693–1701, doi:10.3762/bjoc.13.163

Graphical Abstract
  • the nanoparticle synthesis avoiding the aggregation of nanoparticles, which would lower the surface area and increases the diffusion distances in the final particles for Na or Li ions. For the in situ nanoparticle synthesis TiCl4 was dissolved in benzyl alcohol and the block copolymer was added and
  • polymeric ligand was dissolved in 10 mL of DMSO (Sigma-Aldrich) and added to 70 mL of benzyl alcohol (Acros). The content of the flask was heated to 80 °C. The solution was degassed and filled with argon using a Schlenk line. The process was repeated three times. To this argon filled solution 3.2 mL of
  • loss up to 200 °C indicates the presence of the solvent (benzyl alcohol) which was used for the preparation of the particles. A mass loss of 20% can be observed. The black curve shows the functionalized particles after pyrolysis. b) IR spectrum of pure TiO2 particles (black) and the functionalized
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Published 16 Aug 2017

Total synthesis of elansolids B1 and B2

  • Liang-Liang Wang and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2017, 13, 1280–1287, doi:10.3762/bjoc.13.124

Graphical Abstract
  • , 12.6, 9.7, 7.0, 6.9, 5.2, 5.1; HRMS (ESI) m/z: [M + Na]+ calculated for C35H65BO6Si2Na, 671.4310; found, 671.4312. Reduction of ketone 9 and formation of benzyl alcohol A solution of ketone 9 (466.2 mg, 0.79 mmol, 1.0 equiv) in THF (3 mL) was added to a suspension of LiAlH4 (599.2 mg, 15.79 mmol, 20
  • extracted with ethyl acetate. The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting benzyl alcohol (371.7 mg, 0.63 mmol, 80%, d.r. = 3:1) was obtained after flash column chromatography. Separation of diastereomers was achieved by preparative
  • , 131.8, 128.7, 128.3, 128.1, 124.7, 124.1, 123.7, 113.8, 86.7, 81.3, 73.9, 73.5, 64.9, 55.8, 55.3, 52.9, 46.6, 45.3, 38.0, 33.4, 31.1, 26.3, 24.2, 22.7, 21.3, −3.4, −3.3; HRMS (ESI) m/z: [M + Na]+ calculated for C39H48O3SiNa, 615.3270; found, 615.3270. Synthesis of phenol 15 To a solution of the benzyl
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Published 28 Jun 2017

NMR reaction monitoring in flow synthesis

  • M. Victoria Gomez and
  • Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

Graphical Abstract
  • with a line of <1 Hz in ethanol. As a proof-of-concept, the integrated flow system (microreactor-stripline NMR chip) was tested in the acylation of benzyl alcohol with acetyl chloride (Figure 7) using DIPEA as the base. The kinetics were studied by in situ monitoring and it was found that 70
  • experimental setup of the flow system. (a) Microfluidic probe. (b) Microreactor holder. (c) Stripline NMR chip holder. (d) Arrangement of the microfluidic chip in the holder. Reproduced with permission from reference [44]. Copyright 2009 The American Chemical Society. Acetylation of benzyl alcohol. Spectra at
  • (a) 9 s and (b) 3 min. Stoichiometry: benzyl alcohol/DIPEA/acetyl chloride 1:1:1.2. Reproduced with permission from reference [44]. Copyright 2009 The American Chemical Society. a) Design of MICCS and b) schematic diagram of MICCS–NMR [45]. CH2Cl2 solutions of oxime ether and triethylborane were
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Published 14 Feb 2017

Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds

  • Cira Mollings Puentes and
  • Thomas J. Wenzel

Beilstein J. Org. Chem. 2017, 13, 43–53, doi:10.3762/bjoc.13.6

Graphical Abstract
  • -methylbenzylamine (4), β-methylphenethylamine (5), 1-methyl-3-phenylpiperazine (6), ephedrine (7), α-(methylaminoethyl)benzyl alcohol (8), 2-tert-butylamino-1-phenylethanol (9), α-(1-aminoethyl)-4-hydroxybenzyl alcohol (10), tyrosinol (11), 3-dimethylamino-2-methylpropiophenone (12), cis-(2-benzylamino
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Published 06 Jan 2017

Solvent-free, visible-light photocatalytic alcohol oxidations applying an organic photocatalyst

  • Martin Obst and
  • Burkhard König

Beilstein J. Org. Chem. 2016, 12, 2358–2363, doi:10.3762/bjoc.12.229

Graphical Abstract
  • solvent like hydrogen-atom transfer or the formation of byproducts could be excluded. For liquid substrates, some examples for photocatalytic, solvent-free conversions are reported, such as the oxidation of benzyl alcohol to benzaldehyde [4] and the oxidation of benzenes to phenols [5]. Another field of
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Published 09 Nov 2016

Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols

  • Katrina Tait,
  • Oday Alrifai,
  • Rebecca Boutin,
  • Jamie Haner and
  • William Tam

Beilstein J. Org. Chem. 2016, 12, 2189–2196, doi:10.3762/bjoc.12.209

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  • investigated, starting with cyclohexanol, which resulted in a moderate yield of 63% after only 1 day (Table 5, entry 8). When benzyl alcohol was used, no reaction occurred (Table 5, entry 9) and similarly when phenol was used, no reaction occurred and 8a was recovered (Table 5, entry 10). Conclusion In
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Published 14 Oct 2016

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

  • Maurizio Selva,
  • Alvise Perosa,
  • Sandro Guidi and
  • Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

Graphical Abstract
  • alcohols such as benzyl alcohol, cyclopentanol and menthol [74]. Figure 5 shows some examples of the carbonates obtained in the study. The desired products were achieved at temperatures between 90 and 220 °C. These results highlight the excellent activity and selectivity of these catalytic systems
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Published 26 Aug 2016

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  • Mei-Yuan Hsu,
  • Yi-Pei Liu,
  • Sarah Lam,
  • Su-Ching Lin and
  • Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

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  • dithiol acetal side product 9. Inspired by the results obtained in the synthesis of S-2-deoxyglycosides, we explored the use of numerous alcohols as acceptors in order to directly synthesize O-2-deoxyglycosides from glycals. In Table 2 the reaction of glucal 1 and benzyl alcohol (12) under similar
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Published 04 Aug 2016

Selectively fluorinated cyclohexane building blocks: Derivatives of carbonylated all-cis-3-phenyl-1,2,4,5-tetrafluorocyclohexane

  • Mohammed Salah Ayoup,
  • David B. Cordes,
  • Alexandra M. Z. Slawin and
  • David O'Hagan

Beilstein J. Org. Chem. 2015, 11, 2671–2676, doi:10.3762/bjoc.11.287

Graphical Abstract
  • –Smith method [13] as illustrated in Scheme 3. For further elaboration, aldehyde 15 was reduced with NaBH4 in good yield to generate the corresponding benzyl alcohol 19 [14]. Iodination of 19 to generate 20 with HI in chloroform [15] proved superior (95% yield) to the more classical Appel protocol which
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Published 21 Dec 2015

Convenient preparation of high molecular weight poly(dimethylsiloxane) using thermally latent NHC-catalysis: a structure-activity correlation

  • Stefan Naumann,
  • Johannes Klein,
  • Dongren Wang and
  • Michael R. Buchmeiser

Beilstein J. Org. Chem. 2015, 11, 2261–2266, doi:10.3762/bjoc.11.246

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  • prepare poly(dimethylsiloxane) (PDMS), using three different imidazolium-based free NHCs in combination with benzyl alcohol or methanol as initiator [24]. There, polymerizations were conducted at 80 °C for 16 h to achieve conversions of about 85% (1.5 < ÐM < 1.7, 0.1% catalyst loading). Notably, it was
  • stable at room temperature over long periods of time (observed for up to 2 years) without decomposition, exclusion of humidity provided. Polymerization experiments with D4 were conducted solvent-free at elevated temperature (80 °C, 16 h), both in presence and absence of an initiator (benzyl alcohol, BnOH
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Published 20 Nov 2015

Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

  • David W. Manley and
  • John C. Walton

Beilstein J. Org. Chem. 2015, 11, 1570–1582, doi:10.3762/bjoc.11.173

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  • anion in 70 picks up a proton from the surface so producing the resonance stabilized hydroxybenzyl radical in 71. The latter is reduced to the benzyl anion by a second e− from the TiO2 and is then protonated by a neighboring surface OH (72). The benzyl alcohol product is released most likely along with
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Published 09 Sep 2015

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

  • Qinggang Mei,
  • Chun Wang,
  • Zhigang Zhao,
  • Weicheng Yuan and
  • Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 1220–1225, doi:10.3762/bjoc.11.135

Graphical Abstract
  • [12], antidepressant-like [13] and multidrug resistance reversal [14] activities. Although icariin exerts a variety of important bioactivities, reports concerning its synthesis are very scarce. One Chinese patent reported a 15-step total synthesis of icariin from benzyl alcohol with 0.6% overall yield
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Published 20 Jul 2015

Photocatalytic nucleophilic addition of alcohols to styrenes in Markovnikov and anti-Markovnikov orientation

  • Martin Weiser,
  • Sergej Hermann,
  • Alexander Penner and
  • Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2015, 11, 568–575, doi:10.3762/bjoc.11.62

Graphical Abstract
  • –SH full conversion was achieved within six hours, whereas 40 mol % only reached 70% of conversion at that time. Nucleophilic addition of a variety of alcohols to substrate 1 gave the corresponding products in excellent yields (Table 1). Especially the conversion of 1 with benzyl alcohol was
  • significantly slower, since longer irradiations were needed. Only the addition of phenol failed completely. Since isopropanol and tert-butanol as sterically demanding nucleophiles gave the corresponding addition products in good yields, it was assumed that the acidity of benzyl alcohol, and more significantly
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Published 27 Apr 2015
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