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Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to give dibenzyl ether. In organic synthesis, benzyl chloride is used to introduce the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester. Benzoic acid (C 6 H 5 ...
In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides. Menshutkin-reaction. The reaction is the method of choice for the preparation of quaternary ammonium salts. [1]
synthesis of benzamide from benzoyl chloride and a phenethylamine; synthesis of flutamide, a nonsteroidal antiandrogen; acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid.
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] The trisubstituted benzotrichloride is used for the hydrolysis ...
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).
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 ]
In IUPAC nomenclature, the prefix benzyl refers to a C 6 H 5 CH 2 substituent, for example benzyl chloride or benzyl benzoate. Benzyl is not to be confused with phenyl with the formula C 6 H 5 . The term benzylic is used to describe the position of the first carbon bonded to a benzene or other aromatic ring.
Typically, alkyl nitriles are formed via S N 1 or S N 2-type cyanation with alkyl electrophiles. Illustrative is the synthesis of benzyl cyanide by the reaction of benzyl chloride and sodium cyanide. [1]