Stearic Acid → Stearoyl chloride

Participants

Reaction Steps

A solution of oxalyl chloride (53.5 g, 422 mmol) in 150 mL of chloroform was added drop wise to a solution of stearic acid (30.0 g, 105 mmol) in 250 mL of chloroform. After stirring overnight at ambient temperature the solution was concentrated and co-evaporated twice with chloroform. Drying under vacuum for 1 hour yielded a quantitative yield of a white solid. 1H-NMR (CDCl3): δ=2.85 (t, 2H), 1.70 (q, 2H), 1.30 (m, 28H), 0.85 (t, 3H) ppm. 13C-NMR (CDCl3): δ=173.6, 47.1, 31.9, 29.7, 29.7, 29.6, 29.5, 29.4, 29.3, 29.1, 28.4, 25.1, 22.7, 14.1 ppm. FT-IR: ν=2292, 2853, 1799 (C═O stretch), 1466, 953, 720, 680 cm−1.

Provenance & Evidence