Water → 2-Hydroxymethyl-8-methoxy-chroman

Participants

Reaction Steps

59.0 g (0.25 mol) of ethyl 8-methoxy-chroman-2-carboxylate in 525 ml of anhydrous tetrahydrofuran are added dropwise to a suspension of 9.5 g (0.25 mol) of lithium aluminium hydride in 525 ml of anhydrous diethyl ether at 20° C. in the course of 1 hour, while stirring. The mixture is stirred overnight, and 9.5 ml of water, 9.5 ml of 15% strength sodium hydroxide solution and 28.4 ml of water are then added dropwise in succession, while cooling. The organic phase is decanted and evaporated. The residue is recrystallised twice from methylene chloride/petroleum ether.

Provenance & Evidence