Thionyl Chloride → 1-Isopropyl-3-oxocyclopentanoyl chloride

Participants

Reaction Conditions

Reaction Steps

A solution of 1-isopropyl-3-oxocyclopentylcarboxylic acid (20.1 g, 118.9 mmol) in benzene (150 mL) was slowly treated with thionyl chloride (23.5 mL, 322.1 mmol) and the resulting solution was stirred at 45° C. for 3 hours. The solvent and the volatile components were evaporated under reduced pressure (100 torr) and the residue was distilled to obtain 6.727 g (30%) of the desired product, B.P.: 110-114° C. at 5 torr. 1H NMR (500 MHz, CDCl3): 2.82 (dd, J=18.36, 1.76 Hz, 1H), 2.50 (m, 1H), 2.35 (m, 2H), 2.20 to 190 (bm, 3H), 1.03 (bd, J=8.2 Hz, 6H).

Provenance & Evidence