Hydrochloric Acid → 4'-Phenylthio-2,4-dihydroxybenzophenone

Participants

Reaction Conditions

Reaction Steps

To 50 grams of 4′-chloro-2,4-dihydroxybenzophenone and 27.8 grams of potassium carbonate in 50 mL of 1-methyl-2-pyrrolidinone (NMP)is added 22.2 grams of thiophenol. The resulting suspension is heated at 200° C. with strrring for 2.5 hours. The reaction mixture is then allowed to cool to room temperature, made acidic with 10% aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase is washed with water and brine, dried over anhydrous magnesium sulfate and concentrated to leave 70 grams of a deep red syrup. The crude material is dissolved in an ethyl acetate/heptane mixture (1:1) and partially purified by filtration through a bed of silica gel to yield after concentration 66.6 grams of a light orange solid; 1H NMR and IR data are consistent with the tide compound; Mass. Spec m/z 322 (M+).

Provenance & Evidence