Hydrochloric Acid → Bicyclo(2.2.1)hept-5-ene-2-methanol

Participants

Reaction Steps

A solution of sodium borohydride (15.49 g, 0.409 mol) in absolute ethanol (350 ml) was added dropmise to a stirred solution of bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (50.0 g, 0.409 mol) in absolute ethanol (300 ml) at 50°-60°. Following the addition, the reaction mixture was stirred at ambient temperature for 4 h. The solution was then acidified to congo red with dilute hydrochloric acid (2M), filtered, and this solution was reduced to low volume under reduced pressure. Water (200 ml) was then added, and the mixture was stirred, when a white solid separated. The reaction mixture was filtered, and the aqueous solution was then extracted with ether (3×150 ml). The ether extracts were combined and dried (MgSO4), and the solution was then concentrated under reduced pressure to afford a pale yellow oil. Distillation of the oil gave bicyclo[2.2.1]hept-5-ene-2-methanol, b.p. 98°-100°/15 mm Hg.

Provenance & Evidence