Phenol → HCID 70445962, compound

Participants

Reaction Steps

The above mixture was suspended in 600 ml of 48% hydrobromic acid and excess phenol. The suspension was refluxed for 1 hr and was cooled to room temperature. The reaction mixture was made basic with 50% aqueous sodium hydroxide and the basic solution was extracted with methylene chloride. The methylene chloride extract was extracted with 2M sulfuric acid. The acidic aqueous phase was made basic with 50% sodium hydroxide and the basic solution was extracted with methylene chloride. This last methylene chloride solution was dried over magnesium sulfate and the solvent was removed in vacuo to give the free base: 3-(phenylthio)piperidine as an oil. The free base was reacted with maleic acid and the maleate salt was recrystallized from methanol-diethyl ether as white crystals, m.p. 117°-119° C.

Provenance & Evidence