Hydrochloric Acid → 4-tert-Butyl-2-chlorocyclohexan-1-one

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Reaction Steps

The compound 4-t-butylcyclohexanone, 154.3 grams, is dissolved in 1 liter of benzene to which a trace of ferric chloride is added. The mixture is heated and 148.5 grams of sulfuryl chloride is added dropwise in periodic increments. The reaction mixture is slowly heated to its reflux temperature and maintained at that temperature until no further evolution of hydrochloric acid is observed. The solvent is removed in vacuo and the residue dissolved in a small amount of heptane. The solution is passed through an alumina column and the eluate removed by evaporation under reduced pressure to yield 167.6 grams of crude 4-t-butyl-2-chlorocyclohexanone.

Provenance & Evidence