Acetone → Ethyl 2-[4-(2-benzyloxyethyl)phenoxy]-2-methylpropionate

Participants

Reaction Steps

To a stirred solution of 4-(2-benzyloxyethyl)phenol (420 mg) and 1,1,1-trichloro-2-methyl-2-propanol hydrate (690 mg) in acetone (5 ml) was added potassium hydroxide (320 mg) three times (total 960 mg) at intervals of 10 minutes under ice-cooling, and the mixture was stirred for 16 hours at room temperature. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ice-water and washed with diethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. A solution of thionyl chloride (400 μl) in ethanol (10 ml) was added to the residue, and the mixture was heated under reflux for 6hours. After the reaction mixture was concentrated under reduced pressure, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=5/1) gave ethyl 2-[4-(2-benzyloxy-ethyl)phenoxy]-2-methylpropionate (485 mg).

Provenance & Evidence