Methane, dichloromethoxy- → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

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Reaction Steps

To a solution of 1,2,3,4-tetramethoxy-5-methylbenzene (20.0 g) in methylene chloride (100 ml) was dropwise added titanium tetrachloride (20.6 ml) with cooling with ice, followed by addition of 1,1-dichlorodimethylether (11.0 ml) with cooling with ice. The reaction mixture was allowed to warm to room temperature and further stirred for 8 hr. The reaction mixture was poured into ice-water, and extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to give the entitled compound(21.5 g) as an oil.

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