Acetic Acid → 1-(5-Chloro-2,4-dihydroxyphenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

Acetic acid (17.5 ml) was added dropwise to a suspension of 4-chlorobenzene-1,3-diol (20 g, 0.138 mol) in BF3.OEt2 (100 ml) under a nitrogen atmosphere. The reaction mixture was stirred at 90° C. for 3.5 h and then allowed to cool to RT, causing a solid to precipitate. The mixture was poured into a 10% w/v aqueous sodium acetate solution (350 ml). This mixture was then stirred vigorously for 2.5 h to afford a light brown solid, which was filtered, washed with water, and air-dried overnight to afford the title compound 1-(5-chloro-2,4-dihydroxyphenyl)-ethanone (11.3 g, 44%).

Provenance & Evidence