Acetone → Benzyl 3,4,5-tris(benzyloxy)benzoate

Participants

Reaction Steps

A mixture of gallic acid (4 g, 21.27 mmol), benzyl chloride (19.5 mL, 0.170 mol), tertiary butyl ammonium iodide (catalytic) and K2CO3 (14.67 g, 106 mmol) in acetone (50 mL) was refluxed for 6 h. The mixture was filtered and the filter cake was washed well with acetone. The combined filtrate and washing solvent were evaporated to dryness in vacuo. The residue was dissolved in ethyl acetate (50 mL), washed with H2O (20×2 mL) and brine (30 mL), dried over Na2SO4 and evaporated to dryness. The crude residue was purified by silica gel column chromatography using 5% ethyl acetate in hexane as eluent to obtain pure 1a as white solid (9.01 g, 80%).

Provenance & Evidence