N-Hydroxyphthalimide → N-(3-trifluoromethylbenzyloxy)phthalimide

Participants

Reaction Conditions

Reaction Steps

A solution of 8.0 grams (0.049 mole) of N-hydroxyphthalimide and 4.0 grams (0.059 mole) of sodium acetate in about 25 mL of dimethyl sulfoxide was stirred, and a solution of 11.5 grams (0.059 mole) of 3-trifluoromethylphenylmethyl chloride in about 15 mL of dimethyl sulfoxide was added dropwise during a 10 minute period. Upon completion of addition, the reaction mixture was heated to about 60° C. where it stirred until there was no apparent color change in the reaction mixture. The reaction mixture was then poured into an ice-water mixture. The resultant solid was collected and washed with water. The solid was then recrystallized with 100 mL of ethanol. The solid was collected by filtration and dried, yielding 12.2 grams of N-(3-trifluoromethylphenylmethoxy)phthalimide, mp 106°-108° C. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence