1-Octanol → Octyl 1-chloroethyl carbonate

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of dry n-octanol (6.42 g, 49.3 mmol) and pyridine (3.90 g, 49.3 mmol) in anhydrous ether (75 mL) was added at 0° C. alpha-chloroethyl chloroformate (prepared according to U.K. Pat. No. 1,426,717; 7.00 g, 49.3 mmol). The mixture was stirred vigorously for three hours at 25° C. then filtered. The filtrate was concentrated in vacuo and distilled at 102°-107° C. (2 mm) affording 8.1 g title product as a clear oil (34.2 mmol, 69.4%): 1H NMR (CDCl3) delta 0.44-2.03 (m, 15H), 1.60 (d, J=6 Hz, 3H), 3.94 (t, J=7 Hz, 2H), 6.18 (q, J=6 Hz, 1H).

Provenance & Evidence