Sodium Methoxide → HCID 22494732, compound

Participants

Reaction Steps

A solution of methyl 4-[7-bromo-n-heptyloxy)benzoate (2.3 g) in methanol (50 ml) and a solution of 28% sodium methoxide in methanol (3.5 ml) was refluxed for 12 hours with stirring. The reaction mixture was concentrated under reduced pressure and water was added to the residue and adjusted to pH 1 using hydrochloric acid. The precipitates were collected by filtration, washed with water and dried in vacuo to give an oil. The oil was subjected to column chromatography on silica gel (silica gel 60 F254, Merck: 100 g) and eluted with a mixture of ethyl acetate and n-hexane (1:5). The fractions containing the objective compound were combined and concentrated under reduced pressure to give methyl 4-(7-methoxyheptyloxy)benzoate (1.6 g) as an oil.

Provenance & Evidence