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

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

Graphical Abstract
  • suggested that the coupling occurs through oxidation of benzyl alcohol to benzaldehyde. Alcohols (OH-reagents) are taken in a twofold molar excess [96] or are used as solvents [96][97]; the reaction time is 20–40 h at 45–80 °C. The aerobic oxidative coupling of aldehydes or primary alcohols as CH-reagents
  • [140]. It was proposed that under the reaction conditions benzyl alcohol 135 is oxidized to carboxylic acid 138, while alkylarene gives iodide 139; the nucleophilic substitution between the carboxylate anion and benzyl iodide affords coupling product 137 [140] (Scheme 27). This mechanism differs from
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Published 20 Jan 2015

Synthesis of modified cyclic and acyclic dextrins and comparison of their complexation ability

  • Kata Tuza,
  • László Jicsinszky,
  • Tamás Sohajda,
  • István Puskás and
  • Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 2836–2843, doi:10.3762/bjoc.10.301

Graphical Abstract
  • /7.7 g, respectively (90–95%). 1-O-Benzyl-peracetyl-maltooligomers with slight modification of [15]: Acetobromo-G6, G7 and G8 maltooligomers (3 mmol) were dissolved in benzyl alcohol (BnOH, 120 mmol), freshly prepared dry silver carbonate (6 mmol) was added and the suspensions were stirred in the dark
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Letter
Published 02 Dec 2014

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

  • Véronique Nardello-Rataj and
  • Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

Graphical Abstract
  • -hydroxybenzoate, benzyl alcohol, 2-phenoxyethanol) [45]. The authors established a clear relationship between the binding constants and the antimicrobial activity of the preservatives on various strains: Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli and C. albicans. Indeed, highly water-soluble
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Published 07 Nov 2014

P(O)R2-directed Pd-catalyzed C–H functionalization of biaryl derivatives to synthesize chiral phosphorous ligands

  • Rong-Bin Hu,
  • Hong-Li Wang,
  • Hong-Yu Zhang,
  • Heng Zhang,
  • Yan-Na Ma and
  • Shang-dong Yang

Beilstein J. Org. Chem. 2014, 10, 2071–2076, doi:10.3762/bjoc.10.215

Graphical Abstract
  • (20 mol %), AgOAc (1.5 mmol), TFE (3.0 mL), 100 °C, 24 h, air atmosphere; bSubstrate (0.3 mmol), PhI(OAc)2 (0.9 mmol), Pd(OAc)2 (10 mol %), TFE (3.0 mL), 100 °C, 24 h, air atmosphere; cSubstrate (0.3 mmol), TBHP (1.2 mmol), benzyl alcohol (0.75 mmol), Pd(TFA)2 (10 mol %), DCE (3.0 mL), 60 °C, air
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Published 02 Sep 2014

Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

  • Mahesh K. Lakshman,
  • Manish K. Singh,
  • Mukesh Kumar,
  • Raghu Ram Chamala,
  • Vijayender R. Yedulla,
  • Domenick Wagner,
  • Evan Leung,
  • Lijia Yang,
  • Asha Matin and
  • Sadia Ahmad

Beilstein J. Org. Chem. 2014, 10, 1919–1932, doi:10.3762/bjoc.10.200

Graphical Abstract
  • shown in Scheme 6. Because the guanidinum forms of HBTU and HATU have lower reactivity than the uronium forms [40] slightly more forcing conditions may be needed to obtain satisfactory reactivity. Consistent with this, compound 2c was obtained in 83% yield from a reaction of benzyl alcohol, HATU, and
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Published 19 Aug 2014

Multicomponent reactions in nucleoside chemistry

  • Mariola Koszytkowska-Stawińska and
  • Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

Graphical Abstract
  • obtained in the presence of 4 Å molecular sieves. The analysis of the reaction products showed that ytterbium triflate induced partial 1,2-elimination of benzyl alcohol from the ribosyl residue of the starting aldehyde 86, consequently leading to the 1',2'-didehydro-derivative of the target product 87
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Published 29 Jul 2014

Concise, stereodivergent and highly stereoselective synthesis of cis- and trans-2-substituted 3-hydroxypiperidines – development of a phosphite-driven cyclodehydration

  • Peter H. Huy,
  • Julia C. Westphal and
  • Ari M. P. Koskinen

Beilstein J. Org. Chem. 2014, 10, 369–383, doi:10.3762/bjoc.10.35

Graphical Abstract
  • poorly. Nevertheless, washing of an aqueous solution of the polar lithium salts of 2 (crude 2 in aq. LiOH) with organic solvents of increasing polarity (Et2O→EtOAc) allowed to remove BnOH almost completely (<10% of BnOH referred to 2). Residual benzyl alcohol diminished the yield in the following
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Published 11 Feb 2014

Tuning the interactions between electron spins in fullerene-based triad systems

  • Maria A. Lebedeva,
  • Thomas W. Chamberlain,
  • E. Stephen Davies,
  • Bradley E. Thomas,
  • Martin Schröder and
  • Andrei N. Khlobystov

Beilstein J. Org. Chem. 2014, 10, 332–343, doi:10.3762/bjoc.10.31

Graphical Abstract
  • -dichlorobenzene (ODCB). To link the C60 and C70 fulleropyrrolidines within asymmetric triads with an oxalate spacer we attempted a similar stepwise approach as reported for compounds 1–3 (Scheme 2). Oxalic acid monobenzyl ester monochloride was prepared by equimolar reaction of oxalyl chloride and benzyl alcohol
  • °C, and anhydrous benzyl alcohol (1.4 mL) added dropwise over 15 min. After the addition of the alcohol was completed, the reaction mixture was warmed up to room temperature and stirred for 1.5 h. The resulting mixture was analysed by 1H and 13C NMR spectroscopy and found to be a mixture of the
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Published 05 Feb 2014

Recent applications of the divinylcyclopropane–cycloheptadiene rearrangement in organic synthesis

  • Sebastian Krüger and
  • Tanja Gaich

Beilstein J. Org. Chem. 2014, 10, 163–193, doi:10.3762/bjoc.10.14

Graphical Abstract
  • underwent Curtius rearrangement upon heating. The intermediate isocyanate was intercepted by benzyl alcohol to provide secondary Cbz-protected amine 192. Bredereck’s reagent (193) [162] was used to generate enamine 194. The enol-form of the remaining carbonyl moiety was transformed into the corresponding
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Published 16 Jan 2014

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

  • Mark C. Bagley,
  • Vincenzo Fusillo,
  • Robert L. Jenkins,
  • M. Caterina Lubinu and
  • Christopher Mason

Beilstein J. Org. Chem. 2013, 9, 1957–1968, doi:10.3762/bjoc.9.232

Graphical Abstract
  • benzyl alcohol oxidation [27], the esterification of benzoic acid in a microwave tubular flow reactor [28], a continuous flow recycle microwave reactor for homogeneous and heterogeneous processes [29], a mesoscale flow reactor utilizing Fe3O4 as a microwave absorbing packed reactor bed with internal
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Published 30 Sep 2013

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

  • André S. Kelch,
  • Peter G. Jones,
  • Ina Dix and
  • Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

Graphical Abstract
  • original synthesis were never fully published [9]. This missing information will be presented in this publication (see Supporting Information File 1). The Tolbert synthesis of 16 is summarized in Scheme 2. The crucial intermediate 5-[(benzyloxy)methyl]cyclopentadiene (12) was first prepared from benzyl
  • alcohol (9) via the chloro ether 10 and cyclopentadienylthallium (11) according to a route developed by Corey and co-workers in their prostaglandin work [10]. Cycloaddition of maleic anhydride (MA) to 12 subsequently afforded the endo-adduct 13, which after esterification provided the diester 14 in
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Published 19 Aug 2013

A Lewis acid-promoted Pinner reaction

  • Dominik Pfaff,
  • Gregor Nemecek and
  • Joachim Podlech

Beilstein J. Org. Chem. 2013, 9, 1572–1577, doi:10.3762/bjoc.9.179

Graphical Abstract
  • -nitrobenzyl alcohol (21, Table 2, entry 5) and 4-hydroxymethylbenzoic acid (26, Table 2, entry 6) were reacted with benzyl cyanide or acetonitrile and even with acrylonitrile. A protection of the carboxylic acid turned out to be not necessary. In contrast, a 4-methoxy-substituted benzyl alcohol 52, i.e., an
  • electron-rich benzyl alcohol, furnished no carboxylic ester at all (Table 2, entry 15). Rather poor yields of the respective carboxylic esters were achieved, when unsubstituted benzyl alcohol (56) or 4-fluorobenzyl alcohol (64) were reacted with one of the carbonitriles (Table 3). Instead we isolated
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Published 02 Aug 2013

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

  • Nida Ambreen,
  • Ravi Kumar and
  • Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

Graphical Abstract
  • shortened reaction times. Several other oxidative processes have already been reported in flow chemistry [16]. Results and Discussion Benzyl alcohol was chosen as a substrate in order to examine the efficiency of the reaction and the microreactor flow system. In a batch reaction, the mixture of benzyl
  • of two syringes driven by a syringe pump, a T-connector and a tubing reactor (PTFE tubing, length: 4 m, internal diameter: 0.75 mm) was used for the oxidation of benzyl alcohol to benzaldehyde. The tubing reactor was inserted in a water bath at constant temperature as shown in Figure 1. In all flow
  • optimized reaction time of 4.5 min was then used to convert also a larger amount of benzyl alcohol (15 mmol) to benzaldehyde, which was isolated as the reaction product in 49% yield. These results provide further evidence that this flow process is effective for oxidation methods initially discovered and
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Published 17 Jul 2013

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

  • Lucio Melone and
  • Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

Graphical Abstract
  • absence of light, cumene was completely inert, thus proving the intervention of the catalysts in the oxidative cycle. This process was successfully employed in the selective oxidation of benzyl alcohol at room temperature, affording the corresponding aldehyde in 4 h, in accordance with the results
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Published 02 Jul 2013

Aqueous reductive amination using a dendritic metal catalyst in a dialysis bag

  • Jorgen S. Willemsen,
  • Jan C. M. van Hest and
  • Floris P. J. T. Rutjes

Beilstein J. Org. Chem. 2013, 9, 960–965, doi:10.3762/bjoc.9.110

Graphical Abstract
  • by HPLC analysis. An excess of benzaldehyde was used, because it was also partially reduced to benzyl alcohol in a side reaction. The optimal pH appeared to be 5, comparable with a similar catalyst published by Fukuzumi [29][30]. In the presence of the nondendritic catalyst 3, formation of the N
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Published 17 May 2013

Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides

  • Magnus Liljenberg,
  • Tore Brinck,
  • Tobias Rein and
  • Mats Svensson

Beilstein J. Org. Chem. 2013, 9, 791–799, doi:10.3762/bjoc.9.90

Graphical Abstract
  • of carbocyclic as well as heterocyclic fluorinated substrates [4][5]. Anionic nucleophiles (anions of methanol, benzyl alcohol and hydrogen sulfide) were investigated, as well as neutral nucleophiles (amines). The accuracy was well within 1 kcal/mol and the predictions can be used in a quantitative
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Published 23 Apr 2013

1-n-Butyl-3-methylimidazolium-2-carboxylate: a versatile precatalyst for the ring-opening polymerization of ε-caprolactone and rac-lactide under solvent-free conditions

  • Astrid Hoppe,
  • Faten Sadaka,
  • Claire-Hélène Brachais,
  • Gilles Boni,
  • Jean-Pierre Couvercelle and
  • Laurent Plasseraud

Beilstein J. Org. Chem. 2013, 9, 647–654, doi:10.3762/bjoc.9.73

Graphical Abstract
  • of ε-caprolactone (ε-CL) and rac-lactide (rac-LA) under solvent-free conditions and using 1-n-butyl-3-methylimidazolium-2-carboxylate (BMIM-2-CO2) as precatalyst is described. Linear and star-branched polyesters were synthesized by successive use of benzyl alcohol, ethylene glycol, glycerol and
  • precatalyst. Results and Discussion Two solvent-free polymerization procedures were developed in this study, named methods A and B (Scheme 1). Four initiator alcohols, with an increasing number of OH functions, were successively used: benzyl alcohol (1), ethylene glycol (2), glycerol (3) or pentaerythritol (4
  • and form linear (benzyl alcohol, ethylene glycol) and star-branched (glycerol, pentaerythritol) polyesters. In comparison to their linear analogues, star-branched polymers feature lower crystallinity, lower melt viscosities and smaller hydrodynamic volume [56][57][58]. The crystallinity (defined
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Published 03 Apr 2013

Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines

  • Alan Armstrong and
  • Alexandra Ferguson

Beilstein J. Org. Chem. 2012, 8, 1747–1752, doi:10.3762/bjoc.8.199

Graphical Abstract
  • for further functionalisation of this substrate. Reaction of benzyl alcohol yielded the β-benzyloxy amino-acid derivative 2e in 46%. The orthogonal benzyl protection could allow the free alcohol to be accessed selectively by hydrogenation protocols, leaving the tert-butyl ester intact. Products 2d and
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Published 12 Oct 2012

Palladium-catalyzed substitution of (coumarinyl)methyl acetates with C-, N-, and S-nucleophiles

  • Kalicharan Chattopadhyay,
  • Erik Fenster,
  • Alexander J. Grenning and
  • Jon A. Tunge

Beilstein J. Org. Chem. 2012, 8, 1200–1207, doi:10.3762/bjoc.8.133

Graphical Abstract
  • halomethylcoumarin and highly stabilized nucleophiles or amines [6][7][8][9][10][11][12][13][14][15]. Due to the sensitivity and toxicity of related benzyl halides, there has been interest in catalytically activating hydroxymethylarene and heteroarenes (e.g., benzyl alcohol derivatives) toward reactions with
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Published 27 Jul 2012

Multistep organic synthesis of modular photosystems

  • Naomi Sakai and
  • Stefan Matile

Beilstein J. Org. Chem. 2012, 8, 897–904, doi:10.3762/bjoc.8.102

Graphical Abstract
  • diphosphonates [20][21] for tetravalent anchoring on the ITO surface. The geminal diphosphonates 7 were synthesized from methylene bis(phosphonic dichloride) 8 (Scheme 1) [20][21]. Conversion with benzyl alcohol and pyridine as a base yielded tetrabenzyl methylene bisphosphonate 9. Activation with sodium hydride
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Published 19 Jun 2012

Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

  • Toshiki Nokami,
  • Akito Shibuya,
  • Yoshihiro Saigusa,
  • Shino Manabe,
  • Yukishige Ito and
  • Jun-ichi Yoshida

Beilstein J. Org. Chem. 2012, 8, 456–460, doi:10.3762/bjoc.8.52

Graphical Abstract
  • (Table 2). In accordance with our previous results [26][29], high β-selectvity was observed with highly reactive alcohols (Table 2, entries 1 and 2). On the other hand, less nucleophilic alcohols, such as benzyl alcohol and CF3CH2OH, gave the corresponding glycosides in lower β-selectivity than methanol
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Published 28 Mar 2012

Development of the titanium–TADDOLate-catalyzed asymmetric fluorination of β-ketoesters

  • Lukas Hintermann,
  • Mauro Perseghini and
  • Antonio Togni

Beilstein J. Org. Chem. 2011, 7, 1421–1435, doi:10.3762/bjoc.7.166

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  • -dimethylaniline and benzyl alcohol yielding (+)-10-F in 77% yield (84.9% ee by HPLC), whose configuration has already been established by correlation with 12-F. Comparison of the elution order on a chiral HPLC column with the (+)-sign of the optical rotation implied an (S)-configuration of this sample, and
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Published 17 Oct 2011

Recent advances in the gold-catalyzed additions to C–C multiple bonds

  • He Huang,
  • Yu Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

Graphical Abstract
  • alcohols has been developed by utilizing NaAuCl4. The benzylic and secondary alcohols (55 and 58) worked well under mild conditions with low catalyst loading (Scheme 11). The chiral benzyl alcohol 60 gave racemic ether 61, which suggested the intermediacy of a carbocation. Ye et al. reported an expedient
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Published 04 Jul 2011

Construction of cyclic enones via gold-catalyzed oxygen transfer reactions

  • Leping Liu,
  • Bo Xu and
  • Gerald B. Hammond

Beilstein J. Org. Chem. 2011, 7, 606–614, doi:10.3762/bjoc.7.71

Graphical Abstract
  • rearrangement of alkynyl arylaldehydes 13 to benzoxepinones 14 with good regioselectivity (Scheme 11) [47]. This transformation was effectively promoted by the addition of benzyl alcohol and the sequential addition of p-toluenesulfonic acid. However, in the absence of p-toluenesulfonic acid, benzyl ether 15 was
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Published 13 May 2011

Photocycloaddition of aromatic and aliphatic aldehydes to isoxazoles: Cycloaddition reactivity and stability studies

  • Axel G. Griesbeck,
  • Marco Franke,
  • Jörg Neudörfl and
  • Hidehiro Kotaka

Beilstein J. Org. Chem. 2011, 7, 127–134, doi:10.3762/bjoc.7.18

Graphical Abstract
  • , isoxazole-carbonyl photocycloaddition products constitute another class of photochromic T-type systems (Scheme 7) [18]. Hydrogenation of 9a by palladium/charcoal did not lead to the expected aminoketone 10, but to the enamino ketone 11 and benzyl alcohol, indicating decomposition of 9a back to the starting
  • treatment with lithium aluminium hydride (3 equiv) yielded complex mixtures with benzyl alcohol as one of the main components. By contrast, no reaction could be observed in presence of sodium borohydride or sodium cyanoborohydride. Attempted reduction with sodium triacetoxyborohydride led to decomposition
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Published 26 Jan 2011
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