Potassium bisulfate → HCID 68139172, compound

Participants

Reaction Steps

One part of potassium bisulfate and 25.3 parts of 2-(4-chloro-2-fluorophenyl)-2,3,4,5,6,7-hexahydro-3-hydroxy-3-ethyl-1H-isoindol-1-one were heated with occasional stirring in an oil bath at 160°-170° for 15 minutes. The melt was poured into 200 parts of chloroform and washed successively with 100 parts of water, 50 parts of 10% aqueous sodium chloride solution and 100 parts of saturated aqueous sodium chloride solution. After drying the organic phase with anhydrous sodium sulfate, the solvent was evaporated at 300 mm. Hg at 50° to 22.3 parts of brown, glassy 2-(4-chloro-2-fluorophenyl) -2,3,4,5,6,7-hexahydro-3-ethylidene-1H-isoindol-1-one. The mixture of geometric isomers present was indicated by the absorption in the nuclear magnetic resonance spectrum of 5.1δ (1H, singlet vinyl proton) and 0.95δ (3H, singlet vinyl proton) and 1.3δ (1H, singlet vinyl proton) and 1.3δ (3H, singlet allylic methyl) for the isomer present in 40% of the total mixture.

Provenance & Evidence