Allyl bromide → HCID 67405223, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-hydroxy-2-methylbenzoate (5.46 g, 33 mmol), allyl bromide (4.33 mL, 50 mmol) and cesium carbonate (21.5 g, 66 mmol) in dimethylformamide (60 mL) was stirred at 60° C. for 2.5 hours. The reaction mixture was allowed to cool to room temperature and was then partitioned between water and ethyl acetate. The aqueous portion was extracted twice using ethyl acetate, and the combined organic portion was washed with 5% aqueous lithium chloride, 1N aqueous sodium hydroxide, brine, and then was dried over sodium sulfate, filtered and concentrated in vacuo to afford (6.85 g, 100%) of methyl 2-methyl-3-(prop-2-en-1-yloxy)benzoate as a colorless oil. 1H NMR (400 MHz, DMSO-d6): 7.33-7.30 (m, 1H), 7.27-7.23 (m, 1H), 7.18-7.15 (m, 1H), 6.13-6.02 (m, 1H), 5.35 (dd, 2H), 4.61 (d, 2H), 3.82 (s, 3H), 2.35 (s, 3H). MS (EI) for C12H14O3: 207 (MH+).

Provenance & Evidence