Benzyl 3,4,5-tris(benzyloxy)benzoate → 3,4,5-Tris(benzyloxy)benzoic Acid

Participants

Reaction Steps

To a solution of 1a (4 gm, 7.54 mmol) in ethanol (40 mL), 20% KOH solution (10 mL) was added. The reaction mixture was refluxed for 2 h. Ethanol was evaporated under a vacuo, and was neutralized by 6 N HCL. The combined mixture was extracted in EtOAc (3×20 mL), washed with brine solution (20 mL). The organic layer was dried over Na2SO4 and evaporated to dryness. The crude residue was purified by silica gel column chromatography using 30% ethyl acetate in hexane as eluent to obtain pure compound 3,4,5-tris(benzyloxy)benzoic acid (1b) as white solid (2.78 g, 84%). Rf=0.515 (50% ethyl acetate in hexane)

Provenance & Evidence