Acetyl chloride → Methyl 6-Bromohexanoate

Participants

Reaction Steps

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.

Provenance & Evidence