4-Hydroxybenzoic Acid → (R)-4-(2-n-Hexyloxypropanoyloxy)benzoic acid

Participants

Reaction Steps

To a solution of p-hydroxybenzoic acid (2.15 g, 15.6 mmol) in methylene chloride (30 ml) and pyridine (10 ml), a solution of (R)-2-n-hexyloxypropanoyl chloride (3.0 g, 15.6 mmol) in methylene chloride (20 ml) was added dropwise and then the mixture was refluxed for 7 hours. After cooling, the resultant mixture was taken up in dilute hydrochloric acid, extracted with ethyl ether; the organic extract was washed twice with dilute hydrochloric acid and with H2O for four times, and dried over anhydrous Na2SO4. The solvent was evaporated and the residue was recrystallized from n-hexane to afford 2.13 g of the title compound as white crystals; mp. 67.0°-72.0° C.

Provenance & Evidence