Hydrochloric Acid → 3-Hydroxycaprylonitrile

Participants

Reaction Conditions

Reaction Steps

A 1.9 M solution (21 ml., 40 millimole) of n-butyl lithium in hexane is added cautiously to a stirred solution of freshly distilled diisopropylamine (4.04 g., 40 millimole) in anhydrous tetrahydrofuran (60 ml.) maintained at 0° C. under a nitrogen atmosphere. The resulting solution is stirred at ambient temperature for 15 minutes, cooled to -78° C. and treated with a solution of anhydrous acetonitrile (1.64 g., 40 millimole) in anhydrous tetrahydrofuran (5 ml.). The resulting turbid suspension is stirred and maintained at -78° C. for 30 minutes and then treated with a solution of 1-hexanal (4.0 g., 40 millimole) in anhydrous tetrahydrofuran (5 ml.). After attaining a clear, yellow, reaction solution, cooling at -78° C. is maintained for an additional 15 minutes. The cold reaction solution is treated with 2 N hydrochloric acid (50 ml.) and extracted with ether (100 ml.). The organic extract is washed with water (50 ml.) and 5% aqueous sodium bicarbonate (50 ml.), dried over magnesium sulfate, filtered, and evaporated in vacuo, leaving the title compound as a pale yellow oil (5.2 g., 92%) pmr (CDCl 3) δ 0.97 (3H, t), 2.55 (2H, d), 3.10 (H, s) and 3.93 (H, bs).

Provenance & Evidence