Hydrochloric Acid → HCID 53703849, compound

Participants

Reaction Steps

methyl 4-(bromomethyl)-3-(methyloxy)benzoate (300 mg, 1.15 mmol) was suspended in water (3 ml) and concentrated aqueous hydrochloric acid (380 μl) was added. The reaction mixture was refluxed for 16 h, then cooled to room temperature and partitioned with ethyl acetate (10 ml). The organic phase was separated, washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica gel (dichloromethane:methanol 95:5) to provide 4-(hydroxymethyl)-3-(methyloxy)benzoic acid (74 mg, 35% yield). MS (EI) for C9H10O4: 181(M−H).

Provenance & Evidence