Methane, dichloromethoxy- → 5-Chloro-2-methoxy-3-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

Titanium tetrachloride (24.3 g, 0.128 mole) is added to a solution of 4-chloro-2-methylanisole (10 g, 0.064 mol) in methylene chloride (150 ml) at 0° C. alpha,alpha-Dichloromethyl methyl ether (8.04 g, 0.070 mol) was then added dropwise with stirring over a three minute period at 0° C. The mixture was stirred for 30 minutes at 0° C. then poured into a saturated aqueous solution of sodium bicarbonate (700 ml). The organic layer was then separated and the aqueous phase extracted with methylene chloride. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on a silica gel (300 g) column using hexane-ether (6-1) as eluent. Fractions of 15 ml each were collected. Fractions 21-50 were combined and evaporated in vacuo to a white solid (8.9 g). This solid was rechromatographed on silica gel (300 g), eluting with hexane (15 ml fractions). Fractions 174-215 were combined and evaporated in vacuo to give 2.1 g of the title product as a white solid.

Provenance & Evidence