Hydrochloric Acid → HCID 13366425, compound

Participants

Reaction Steps

A solution of 31.5 (0.15 mol) of 2,3,5-trimethyl-1-trifluoromethoxybenzene, 315 ml of acetic acid, 31.5 ml of concentrated hydrochloric acid, 31.5 ml of aqueous formaldehyde and 13 g (0.185 mol) of chloromethyl methyl ether was heated to 85° C. for 72 hours. (Small samples were worked up periodically after 48 hours to optimize the ratio of monochloromethyl product:dichloromethyl product:starting material). The solution was then cooled, poured into 1.5 liters of water and extracted with 3×500 ml of hexane. The hexane extracts were washed with 1 liter of water and 500 ml of saturated NaHCO3 solution, dried (MgSO4), filtered, and concentrated to give 30 g of crude (4-trifluoromethoxy 2,3,6-trimethylphenyl)methyl chloride containing some starting material, 2,3,5-trimethyl-1-trifluoromethoxybenzene, which was removed by distillation at 24°-30° C./0.05 mm. The residue (22 g), crude (4-trifluoromethoxy-2,3,6-trimethylphenyl)methyl chloride, was used directly in the next step.

Provenance & Evidence