Condensation of Aliphatic Alcohols with Aryl Hydrocarbons in the Presence of Chlorosulfonic Acid¹

Abstract

Oxidation with chromic acid in glacial acetic acid solution yielded a small quantity of acid, m. p. 230-235°. The physical constants checked fairly closely those of />-chlorocumene prepared by a boron fluoride alkylation method in this Laboratory,11 but the discrepancies seemed to indicate that a mixture of isomeric chlorocumenes were present, among which the para predominated.A higher-boiling chlorocumene fraction, b. r. 125-126 (100 mm.), was observed to have d20 0.9816 and m21id 1.5075. The acid derivative was prepared and purified by sublimation, m. p. 239-241 °, checking the literature for ¿ -chlorobenzoic acid.Diisopropylbenzene impurities probably caused the depression of specific gravity and refractive index values.

Synthesis of DDT with Chlorosulfonic Acid as Condensation Agent

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synthesis of DDT with chlorosulfonic acid as the condensation agent in the reaction of chloral hydrate with chlorobenzene was inferred to in three recent articles in the literature (10,11,12). Two of these references (10, 11) disclose the details of a new experimental method and a postulated four-stage reaction mechanism.

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