Hydrochloric Acid → Tryptophol

Participants

Reaction Steps

A stirred suspension of m-cresyl 3-indolylglyoxylate (55.8 g.) and sodium borohydride (22.7 g.) in isopropanol (300 ml.) was slowly heated to reflux and held for 5 hours. The cooled mixture was diluted with water (2 l.), acidified with hydrochloric acid and extracted with dichloromethane. The extract was washed with sodium carbonate solution, dried and evaporated to give a mobile oil smelling strongly of cresol. This was distilled at 0.5 - 1 mm and the fraction collected at 160°-200° vapour temperature was crystallised from toluene (60 ml.), giving tryptophol as white crystals m.p. 57°-59°.

Provenance & Evidence