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Quaternary ammonium salts, used as surfactants, are readily formed by alkylation of tertiary amines with benzyl chloride. [3] 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 ...
The Delépine reaction is the organic synthesis of primary amines (4) by reaction of benzyl or alkyl halides (1) with hexamethylenetetramine (2) followed by acid hydrolysis of the quaternary ammonium salt (3). [1] [2] It is named after the French chemist Stéphane Marcel Delépine (1871–1965). Delepin reaction
Benzyl is commonly used in organic synthesis as a robust protecting group for alcohols and carboxylic acids. Treatment of alcohol with a strong base such as powdered potassium hydroxide or sodium hydride and benzyl halide (BnCl or BnBr) [9] [10]
The reaction is the method of choice for the preparation of quaternary ammonium salts. [1] Some phase transfer catalysts (PTC) can be prepared according to the Menshutkin reaction, for instance the synthesis of triethyl benzyl ammonium chloride (TEBA) from triethylamine and benzyl chloride :
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.
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C 6 H 6 O 3 S.It is the simplest aromatic sulfonic acid.It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
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 ]
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.