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The benzyl alcohol thus formed is quickly converted to the chloride under the reaction conditions. Mechanism of Blanc chloromethylation. Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 +) or chlorocarbenium cation (ClCH 2 +), which may be formed in the presence of zinc chloride. [4]
Industrially, benzyl chloride is the precursor to benzyl esters, which are used as plasticizers, flavorants, and perfumes. Phenylacetic acid , a precursor to pharmaceuticals, is produced from benzyl cyanide , which in turn is generated by treatment of benzyl chloride with sodium cyanide .
For example, benzyl chloroformate is used to introduce the Cbz (carboxybenzyl) protecting group and fluorenylmethyloxycarbonyl chloride is used to introduce the FMOC protecting group. Chloroformates are popular in the field of chromatography as derivatization agents. They convert polar compounds into less polar more volatile derivatives.
Benzyl chloride can also be converted via benzyl cyanide with subsequent hydrolysis into phenylacetic acid. [ 22 ] [ 23 ] The disubstituted benzal chloride is converted to benzaldehyde , a popular flavorant [ 24 ] and intermediate for the production of malachite green and other dyes. [ 25 ]
Benzyl is most commonly abbreviated Bn. For example, benzyl alcohol can be represented as BnOH. Less common abbreviations are Bzl and Bz, the latter of which is ambiguous as it is also the standard abbreviation for the benzoyl group C 6 H 5 C(O)−. Likewise, benzyl should not be confused with the phenyl group C 6 H 5 −, abbreviated Ph.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol. [13] Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties.
2- and 4-chlorotoluene are precursors to the corresponding benzyl chloride (ClC 6 H 4 CH 2 Cl), benzaldehyde (ClC 6 H 4 CHO), and benzoyl chloride (ClC 6 H 4 C(O)Cl). [2] 2- and 4-chlorotoluenes are converted to 2-chlorobenzonitrile and 4-chlorobenzonitrile, respectively. [3] Chlorotoluenes are precursors to dichlorotoluenes.