Citric Acid → 2-Allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoic acid

Participants

Reaction Steps

To a stirred solution of methyl 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoate (2.50 g, 6.39 mmol) from Step 1 above in methanol (40 mL) was added 2N NaOH (15.9 mL, 31.9 mmol). The reaction mixture was refluxed for 30 minutes and cooled in a ice water bath. The solution was acidified with 5% citric acid and the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAC and washed with water (2×75 mL). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure to give 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoic acid as a white solid, which was used without further purification.

Provenance & Evidence