Water → 2-((3,4-Dihydro-2,2-dimethyl-4-phenyl-2H-1-benzopyran-7-yl)oxy)-N,N-dimethylethanamine

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Reaction Steps

A mixture of 2,2-dimethyl-7-hydroxy-4-phenylchroman (3.72g), sodium hydride (0.53g, 60% dispersion in oil) and 2-dimethylaminoethyl chloride (1.58g) in toluene (59 ml) was stirred and boiled under reflux for 6 hours. Water was added to the cooled mixture and the organic layer was separated and extracted with 5N hydrochloric acid (3 × 30 ml). The combined acid extract was basified, extracted with ether and the ether extract dried (magnesium sulphate). Removal of the solvent gave 2,2-dimethyl-7-dimethylaminoethoxy-4-phenylchroman which was isolated as its hydrochloride salt, m.p. 165°-167° C.

Provenance & Evidence