3-Chloro-1-butene → 3-[4-(tert-Butoxycarbonyl)phenoxy]-1-butene

Participants

Reaction Conditions

Reaction Steps

A solution of 1,1-dimethylethyl 4-hydroxybenzoate (5.0 g, 25.7 mmol) in N,N-dimethylformamide (35 ml) was treated with a solution of sodium hydroxide (1.14 g, 35.1 mmol) in water (2 mL). Then 3-chloro-1-butene (3.06 g, 33.8 mmol) was added and the resulting mixture was heated at 45° C. for 5 hours. The cooled mixture was diluted with toluene, washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. Chromatography of the residue on silica gel (elution toluene-hexane, 1:1) gave 3.84 g (60%) of the title material as a clear oil.

Provenance & Evidence