Allyl bromide → Methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate

Participants

Reaction Steps

A mixture of methyl 2-hydroxy-5-isopropyl-4-(methoxymethyloxy)benzoate (995 mg, 3.92 mmol) and anhydrous potassium carbonate (650 mg, 4.71 mmol) in acetonitrile (25 ml) was treated with allyl bromide (0.356 ml, 4.11 mmol) and the mixture was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo, water (30 ml) was added and the organic material was extracted with dichloromethane (2×30 ml). The combined organic extracts were evaporated to dryness in vacuo to afford methyl 2-allyloxy-5-isopropyl-4-(methoxymethyloxy)benzoate (1125 mg, 97%) as pale yellow oil. 1H NMR (DMSO-d6) 7.58 (1H, s), 6.78 (1H, s), 6.03 (1H, m), 5.52 (1H, dm), 5.33 (2H, s), 5.28 (1H, dm), 4.61 (2H, m), 3.78 (3H, s), 3.42 (3H, s), 3.19 (1H, m), 1.18 (6H, d). MS: [M+Na]+ 317.

Provenance & Evidence