Methanol → Methyl 8-bromooctanoate

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.

1. temperaturethe mixture is heated
2. temperatureat reflux temperature for 5 hours
3. customThe solvent is removed
4. dissolutionthe oily residue is dissolved in ether (4 L)
5. washThe solution is washed with water (3×2 L), saturated NaHCO3 solution (1 L) and brine (1 L)
6. dry with materialThe ether portion is dried (MgSO4)
7. filtrationfiltered
8. customto remove dessicant
9. customEvaporation of solvent
10. distillationfollowed by distillation of the crude oil

ORD record

ord-28e7122ea4c948cbba9c039c53293741

Source dataset

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04478842