Hydrochloric Acid → 1-(Trifluoromethyl)cyclopropanemethanol

Participants

Reaction Steps

Treat a cooled solution (0° C.) of 1-(trifluoromethyl)cyclopropanecarboxylic acid (9 g, 58.4 mmol) in Et2O (140 mL) under N2, with LiAlH4 (2.9 g, 76 mmol) portion wise, allow to warm to RT and stir overnight. Re-cool the mixture to 0° C., treat slowly with HCl, warm to RT and separate the layers. Extract the aqueous layer with diethyl ether (2×), wash the combined organics with brine, dry over Na2SO4 and concentrate in a cool (<30° C.) water bath to afford the title compound (7 g, 86% yield). 1H NMR (400 MHz, DMSO-d6): δ 4.94 (t, J=6.0 Hz, 1H), 3.54 (d, J=6.0 Hz, 2H), 0.87-0.84 (m, 2H), 0.81-0.79 (m, 2H).

Provenance & Evidence