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

Participants

Reaction Conditions

Reaction Steps

Titanium tetrachloride (21.6 g, 0.114 mole) was added to a solution of 2-methyl-4-chloroanisole (9 g, 0.057 mole) in methylene chloride at 0° C. Then, 1,1-dichloromethyl methyl ether (7.24 g, 0.063 mole) was added dropwise over a three minute period and the reaction mixture stirred at 0° C. for 30 minutes. The reaction was quenched by carefully pouring it into water (600 ml). The organic layer was separated and the aqueous phase extracted with methylene chloride (2×100 ml). The combined organic layer and extracts was washed with brine, dried (MgSO4) and concentrated under reduced pressure to a pale yellow solid (10.1 g).

Provenance & Evidence