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In particular, he discovered the relations between chlorotoluene and benzyl chloride.
It is created by the reaction of benzyl chloride and sodium hydrosulfide.
This explains why benzyl chloride is a lachrymator and has been used as in chemical warfare.
For example, benzyl chloride gives the phosphonium salt:
Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid.
Benzyl chloride is an alkylating agent.
Phenylpyruvic acid is synthesized from benzyl chloride by double carbonylation (82% yield).
Finally, it can also be prepared by the coupling of benzyl chloride using aluminium chloride as a catalyst.
Benzylamine can be produced through a number of ways, the main industrial route being the reaction of benzyl chloride and ammonia.
The barrier is higher in CS2 than in acetone-d6 solution, in contrast to a molecule like benzyl chloride.
The 1H nmr spectra of benzyl chloride in dilute CS2 and acetone-d6 solutions are analyzed.
Benzyl chloride also reacts readily with metallic magnesium to produce a Grignard Reagent.
The geometry-optimized STO-3G results agree quantitatively with the derived barrier for benzyl chloride.
Benzyl alcohol is prepared by the hydrolysis of benzyl chloride using sodium hydroxide:
Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine:
Condensation of benzyl chloride 1 with ethyl ester of glycine gives alkylated product 2.
The equation predicts that in a nucleophilic displacement on benzyl chloride, the azide anion reacts 3000 times faster than water.
A typical synthesis is for benzalkonium chloride from a long-chain alkyldimethylamine and benzyl chloride:
One manifestation of this enhanced reactivity is the photochemical chlorination of the methyl group in toluene to give benzyl chloride.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula CHCHCl.
Quaternary ammonium salts, used as surfactants, are readily formed by alkylation of tertiary amines with benzyl chloride.
Since benzyl chloride is quite volatile at room temperature, it can easily reach the mucous membranes where the hydrolysis takes place with production of hydrochloric acid.
In an industrial application, about 100,000 tonnes of benzyl chloride are prepared annually by the gas-phase photochemical reaction of toluene with chlorine.
Industrially, benzyl chloride is the precursor to benzyl esters which are used as plasticizer, flavorants, and perfumes.
The column converts benzyl chloride to bibenzyl in a Wurtz coupling and in a similar fashion dibenzothiophene is reduced to biphenyl.