Hydrochloric Acid → 2-(Chloromethyl)anisole

Participants

Reaction Conditions

Reaction Steps

Chloromethylanisole was prepared by placing 162 grams (1.5 mole) of anisole and 150 grams of toluene in a 1-liter round bottom flask which was equipped with a mechanical stirrer, thermowell and gas inlet. The gas inlet was connected by means of a glass tube to a 200 cc round bottom flask also equipped with a gas inlet and thermowell. The glass tube which extended from the smaller flask to the larger flask was surrounded by a heating tape. The 200 cc round bottom flask was charged with 64 grams (2.1 mole) of paraformaldehyde following which the flask was then heated and maintained at a temperature of 120° C. Hydrogen chloride gas was passed at a flow rate of from 200 to 300 cc/min. into the flask containing the anisole and toluene. Likewise, the depolymerized formaldehyde was also passed to the flask containing anisole and toluene at a rate which was sufficient to match the rate of hydrogen chloride addition and also at a rate which was sufficient to prevent repolymerization of the formaldehyde to paraformaldehyde. At the end of 4 hours, the hydrogen chloride gas flow was reduced to 20 ml/min. and thereafter was halted. The reaction product was recovered and subjected to gas-liquid chromatographic analysis which disclosed a 91% conversion of the anisole with a 96.7% selectivity to monochloromethylanisoles.

Provenance & Evidence