Sodium hydride → alpha-Oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester

Participants

Reaction Steps

To a suspension of 0.162 g (4.06 mmol) of 60% sodium hydride on oil in 10 ml of anhydrous DMF was added 0.75 g (3.87 mmol) of 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester. The reaction mixture was stirred at room temperature under argon for 15 minutes and then 1.4 g (4.06 mmol) of 12-phenoxydodecyl bromide in 20 ml of anhydrous DMF was added. The mixture was stirred and heated at 60° for 24 hours. The usual workup followed by chromatography on 45 g of silica gel gave alpha-oxo-4-[(12-phenoxydodecyl)oxy]benzeneacetic acid ethyl ester (83% yield, mp 58°-59°).

Provenance & Evidence