Sodium Iodide → 3-(Octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester

Participants

Reaction Steps

A mixture of 10.0 g (0.02 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 4.3 ml (0.03 mol) of methyl 5-bromovalerate, 5.6 (0.04 mol) of potassium carbonate and 3.0 g (0.02 mol) of sodium iodide in 300 ml of acetone and 75 ml of DMF was stirred at reflux under argon for 40 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from methylene chloride-methanol to give 11.3 g (92% yield, mp 40°-42°) of 3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Provenance & Evidence