Ethyl phenylacetate → Ethyl 4-(1-hydroxyundecyl)phenylacetate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl phenylacetate (13.1 g, 0.08 mol) and aluminium chloride (24.5 g, 0.18 mol) was added undecanoyl chloride (20 ml) at -10° C. The reaction mixture was stirred for 20 minutes at room temperature and further for 4 hours at 50° C., and then poured into the mixture of concentrated hydrochloric acid (40 ml) and ice (160 g). The resultant precipitate was extracted with ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was dissolved in ethanol (100 ml), to which was added sodium borohydride (1.18 g, 0.03 mol). The reaction mixture was stirred at room temperature, to which was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane:ethyl acetate=5:1) to obtain ethyl 4-(1-hydroxyundecyl)phenylacetate (3-v, 10.9 g, 41%) as oil.

Provenance & Evidence