3-Chloro-6-hydroxyacetophenone → (E)-1-(5-chloro-2-hydroxyphenyl)-3-(dimethylamino)prop-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-chloro-2-hydroxyphenyl)ethanone (17.2 g, 100.8 mmol) in propan-2-ol (100 ml) was added 1,1-dimethoxy-N,N-dimethylmethanamine (27 ml, 200 mmol) dropwise and the reaction mixture was warmed to 45° C. and stirred for 24 hours. The resulting suspension was cooled in ice, filtered and washed with propan-2-ol then tert-butyl methyl ether. The solid was dried in vacuo to give the title compound as a bright yellow solid, 16.39 g, 72% yield.

Provenance & Evidence