Alcohol benzylation

Aliy alcohol tert-Butyi alcohol Benzyl alcohol Phenethyi alcohol Ethylene glycol 1,2-Propylene glycol Glycerol Pentaerythritoi Pinacoi Phenol... 

Benzyl Alcohol and p-Phenylethyl Alcohols" ia ECT 1st ed., Vol. 2, pp. 483—489, by H. L. Simons and E. E. Polger, Harold L. Simons, Inc. (Benzyl alcohol), and E. T. Theimer, van Ametingen-Haebler, Inc. (P-Phenylethyl alcohol) "Benzyl Alcohol and P-Phenylethyl Alcohol" ia ECT 2nd ed., pp. 442—449, by William E. Ringk, Benzol Products Company (Benzyl alcohol), and E. T. Theimer, International Elavors Eragrances, Inc. (P-Phenylethyl... 

Benzyioxycarbonyi chioride (Cbz-Ci, benzyi cbioroformate) [501-53-1] M 170.6, b 103 /20mm, d 1.195, n 1.5190. Commercial material is better than 95% pure and may contain some toluene, benzyl alcohol, benzyl chloride and HCl. After long storage (e.g. two years at 4 , Greenstein and Winitz [The Chemistry of the Amino Acids Voi 2 p. 890, J Wiley and Sons NY, 1961] recommended that the liquid should be flushed with a stream of dry air, filtered and stored over sodium sulfate to remove CO2 and HCl which are formed by decomposition. It may further be distilled from an oil bath at a temperature below 85 because Thiel and Dent [Annalen 301 257 1898] stated that benzyioxycarbonyi chloride decarboxylates to benzyl chloride slowly at 100 and vigorously at 155 . Redistillation at higher vac below 85 yields material which shows no other peaks than those of benzyioxycarbonyi chloride by NMR spectroscopy. LACHRYMATORY and TOXIC. 

Catalytic hydrogenolysis of an O-benzyl protective group is a mild, selective method introduced by Bergmann and Zervas to cleave a benzyl carbamate (>NC0-0CH2C6H5 —> >NH) prepared to protect an amino group during peptide syntheses. The method has also been used to cleave alkyl benzyl ethers, stable compounds prepared to protect alkyl alcohols benzyl esters are cleaved by catalytic hydrogenolysis under neutral conditions. 

DMAP, THF, 65% yield. This reaction is selective for primary alcohols. Benzyl, isobutyl, and ethyl carbonates are also prepared using this method (63-85% yield). 

Benzyl alcohol, benzyl esters Benzyl chloride, sodium carbonate/sodium... 

Alcohols. n-Butyl alcohol n-Hexyl alcohol alcohol Benzyl alcohol Glycerol Sucrose. 

Benzyl Alcohols. Benzyl alcohols of nearly all kinds undergo reduction when treated with acid in the presence of organosilicon hydrides. The most obvious exception to this is the behavior of benzyl alcohol itself. It resists reduction by the action of trifluoroacetic acid and triethylsilane, even after extended reaction times.26 Reducing systems consisting of triethylsilane and sulfuric acid/acetic acid or p-toluenesullonic acid/acetic acid mixtures also fail to reduce benzyl alcohol to toluene.134 As previously mentioned, substitution of boron trifluoride for trifluoroacetic acid results in the formation of modest yields of toluene, but only when a very large excess of the silane is used in order to capture the benzyl cation intermediate and suppress Friedel-Crafts oligomerization processes.129,143... 

The availability of non-racemic oxepins through tandem catalytic RCM and Zr-catalyzed kinetic resolution has additional important implications. Optically pure heterocycles that carry a heteroatom within their side chain (cf. (S)-14 in Scheme 3) can be used in stereoselective uncatalyzed alkylations. The alcohol, benzyl ether or MEM-ethers derived from (S)-14 readily undergo directed [10] and diastereoselective alkylations when treated with a variety of Grignard reagents [11]. 

The availability of oxepins that bear a side chain containing a Lewis basic oxygen atom (entry 2, Table 6.4) has further important implications in enantioselective synthesis. The derived alcohol, benzyl ether, or methoxyethoxymethyl (MEM) ethers, in which resident Lewis basic heteroatoms are less sterically hindered, readily undergo diastereoselective uncatalyzed alkylation reactions when treated with a variety of Grignard reagents [17]. The examples shown below (Scheme 6.7) demonstrate the excellent synthetic potential of these stereoselective alkylations. 

Benzyl chloride undergoes all the transformations of the alkyl halides. Hydrolysis with hot aqueous alkalis yields the corresponding alcohol, benzyl alcohol C6H5.CH2OH, a colourless liquid which boils at 206°. (Chap. V. 4, p. 220.)... 

Uses Manufacture of perfumes, benzyl compounds (e.g., benzyl alcohol, benzyl acetate). 

Chemical/Physical. Products identified from the reaction of toluene with nitric oxide and OH radicals include benzaldehyde, benzyl alcohol, 3-nitrotoluene, p-methylbenzoquinone, and o, m, and p-cresol (Kenley et ah, 1978). Gaseous toluene reacted with nitrate radicals in purified air forming the following products benzaldehyde, benzyl alcohol, benzyl nitrate, and 2-, 3-, and 4-nitro-toluene (Chiodini et al., 1993). Under atmospheric conditions, the gas-phase reaction with OH radicals and nitrogen oxides resulted in the formation of benzaldehyde, benzyl nitrate, 3-nitrotoluene, and o-, m-, and p-cresol (Finlayson-Pitts and Pitts, 1986 Atkinson, 1990). 

Benzaldehyde, see Benzyl alcohol. Benzyl chloride. Isopropylbenzene, Naphthalene, Styrene,... 

Photolytic. Photolysis of permethrin in aqueous solutions containing various solvents (acetone, hexane, and methanol) under UV light (1 >290 nm) or on soil in natural sunlight initially resulted in the isomerization of the cyclopropane moiety and ester cleavage. Photolysis products identified were 3-phenoxybenzyldimethyl acrylate, 3-phenoxybenzaldehyde, 3-phenoxybenzoic acid, mono-chlorovinyl acids, cis- and fra/is-dichlorovinyl acids, benzoic acid, 3-hydroxybenzoic acid, 3-hydroxybenzyl alcohol, benzyl alcohol, benzaldehyde, 3-hydroxybenzaldehyde, and 3-hydroxybenzoic acid (Holmstead et ah, 1978). 

Sudocrem benzyl alcohol, benzyl benzoate, benzyl cinnamate, lanolin, zinc... 

Alcohols benzyl, teri-butyl, ethanol, ethylene glycol, glycerol, isopropanol, methanol, propenediol... 

Alkyl bromides, from alcohols, benzyl bromide, and triphenyl phosphite,... 

Benzyl alcohol Benzyl alcohol, which is contained in some of these products as a preservative, has been associated with an increased incidence of neurological and other complications in premature infants that are sometimes fatal. 

Benzyl alcohol Benzyl alcohol, a preservative contained in the diluent supplied, has been associated with a fatal gasping syndrome in premature infants. 

Akylation, of acids, 50, 61 by oxonium salts, 51,144 Alkyl bromides, from alcohols, benzyl bromide, and triphenyl phosphite,... 

---