Methane, dichloromethoxy- → HCID 86682039, compound

Participants

Reaction Steps

A solution of 2′-hydroxy-4′,5′-dimethoxyacetophenone (1.0 g, 5.1 mmol) in methylene chloride (20 mL) was added with dichloromethyl methyl ether (1.6 g, 14 mmol) under an argon atmosphere. Then, the mixture was slowly added with titanium(IV) chloride (2.2 mL, 20 mmol) at 0° C., and then the mixture was refluxed for 18 hours by heating. The reaction mixture was added with ice water, the mixture was extracted with ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (3:1→1:1)) to obtain 3-acetyl-2-hydroxy-5,6-dimethoxybenzaldehyde (0.12 g, 10%).

Provenance & Evidence