Homovanillyl alcohol → 4-Hydroxy-3-methoxyphenethyl chloride

Participants

Reaction Steps

Thionyl chloride (0.5 ml) was added, dropwise, to a! stirred solution of 4-hydroxy-3-methoxyphenethyl alcohol (0.83 g--commercially available) in dichloromethane (50 ml). When the addition was complete, the mixture was heated under reflux for 3 hours. On cooling to room temperature, the mixture was concentrated in vacuo to give a gum which was purified by column chromatography on silica eluting with dichloromethane containing methanol (0% up to 2%). The product-containing fractions were combined and concentrated in vacuo to give the title compound as an oil, yield 0.36 g.

Provenance & Evidence