Hydrochloric Acid → 2,6-Diisopropylbenzenesulfonyl chloride

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Reaction Steps

One equivalent part by weight of 2,6-diisopropylaniline is diazotized with 1.1 equivalent parts of sodium nitrite and 1.1 equivalent parts of hydrochloric acid in acetic acid at 0° to 5°. This solution is added dropwise with stirring to a solution of acetic acid containing 1 equivalent part of cuprous chloride and excess sulfur dioxide at 10°. When the addition is complete and nitrogen evolution ceases, the mixture is poured into ice water and the oily product extracted into ether. The organic layer is washed with water and dried over sodium sulfate. Removal of the solvent gives 2,6-diisopropylbenzenesulfonyl chloride which may be purified by distillation.

Provenance & Evidence