Acetic Acid → 8-Hydroxyoctyl acetate

Participants

Reaction Steps

A solution of 1.987 g (13.7 mmoles) of 1,8-octanediol in 25 ml (441 mmoles) of glacial acetic acid was mixed with 200 ml (11.11 moles) of H2O containing 4 ml (72 mmoles) of conc. H2SO4. This mixture was extracted continuously for 40 hours using hexane. The monoester is not very soluble in hexane and hence a mixture of hexane-cyclohexane (in which the monoester, but not the starting diol, is soluble) should be recommended if one is interested in developing this process for 1,8-octanediol. After cooling the hexane to room temperature, ether was added to make the organic layer homogeneous. The ether-hexane layer was then dried over anhydrous potassium carbonate and filtered. Removal of the solvent under reduced pressure afforded 2.38 g (~92% yield) of product, GC analysis of which indicated the presence of 2% starting diol and 4% diester. The purity of the desired monoester was therefore 94%.

Provenance & Evidence