Acetyl chloride → Methyl 6-Bromohexanoate

To a solution of acetyl chloride (1.0 mL, 14 mmol) in methanol (150 mL) at 0° C. was added a solution of 6-bromohexanoic acid (10.0 g, 51 mmol) in methanol (50 mL). The mixture was heated at reflux for 2 hours, then allowed to cool down to room temperature and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and washed consecutively with saturated aqueous sodium hydrogen carbonate (2×50 mL), distilled water (50 mL), and brine (50 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give the title compound (10.3 g, 96%) as a colourless oil.

1. temperatureThe mixture was heated
2. temperatureat reflux for 2 hours
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
5. washwashed consecutively with saturated aqueous sodium hydrogen carbonate (2×50 mL)
6. distillationdistilled water (50 mL), and brine (50 mL)
7. dry with materialThe organic layer was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-d911f4fc5a96475bae0504e9baf554f5

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2