Methanol → Methyl 8-bromooctanoate

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

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

ORD record

ord-a5c94043cbff4f1eab5b907b3a814fa9

Source dataset

uspto-grants-1984_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04460777