N,N-Dimethylaniline → 5-(Chloromethyl)-1,2,3-trimethoxybenzene

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Reaction Steps

Combine 3,4,5-trimethoxybenzyl alcohol (1.0 g, 5.04 mmol) and N,N-dimethylaniline (0.904 g, 7.46 mmol) in dichloromethane (10 mL). Cool in an ice bath. Add dropwise thionyl chloride (0.904 g, 7.6 mmol). Warm to ambient temperature. After 1 hour, partition the reaction mixture between a 1 M aqueous hydrochloric acid solution and dichloromethane. Separate the layers and extract the organic layer with a saturated solution of sodium bicarbonate. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Provenance & Evidence