Cyclohexaneacetic acid → Cyclohexylacetyl chloride

Participants

Reaction Conditions

Reaction Steps

Cyclohexyl-acetic acid (288 ml, 2.04 mol) and thionyl chloride (306 ml, 4.19 mol) were stirred in a 1000 ml flask fitted with reflux condenser, CaCl2 drying tube, thermometer, heating mantle, and magnetic stirrer. The reaction solution was heated to 50° C. with stirring (gas evolution). After 14.5 hours at 50° C., the reaction mixture was further heated to a gentle reflux for 90 min and then cooled to room temperature. Excess thionyl chloride was removed under reduced pressure. The residual liquid was vacuum distilled to afford cyclohexyl-acetyl chloride (250.92 g, 77%) as a pale yellow liquid. bp.: 60° c./5 mm Hg; MS m/z: 161 (M+H)+.

Provenance & Evidence