Methanol → Methyl 8-bromooctanoate

Participants

Reaction Steps

Methanol (4.7 L), 8-bromooctanoic acid (0.912 kg) and sulfuric acid (0.912 L) are charged into a suitable reactor and the mixture is heated at reflux temperature for 5 hours and is then stirred at ambient temperature overnight. The solvent is removed at reduced (3 mm Hg) pressure and the oily residue is dissolved in ether (4 L). The solution is washed with water (3×2 L), saturated NaHCO3 solution (1 L) and brine (1 L). The ether portion is dried (MgSO4) and filtered to remove dessicant. Evaporation of solvent followed by distillation of the crude oil gives methyl 8-bromooctanoate, b.p. 73°-76°/0.05 mm Hg, nD23 1.4614.

Provenance & Evidence