Ammonium Chloride → 1-(3,4,5,6-Tetramethoxy-2-methylphenyl)-1-(2-benzyloxyphenyl)methanol

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Reaction Steps

Under ice-cooling, into a Grignard reagent (35 ml, a tetrahydrofuran solution) prepared from 2-(benzyloxy)bromobenzene (11.50 g, 0.044 mol) and magnesium (1.16 g, 0.048 mol) was dropped a solution of 3,4,5,6-tetramethoxy-2-methylbenzaldehyde (5.00 g, 0.021 mol) in anhydrous tetrahydrofuran (30 ml) and the mixture was stirred for 2 hours more. The reaction solution was poured into a saturated aqueous solution of ammonium chloride followed by extracting with ether. The extract was washed with a saturated saline and dried. The reaction solution was filtered and the crude product obtained by concentrating the filtrate was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (8.80 g, 0.021 mol, 99%).

Provenance & Evidence