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

HRID 1076123Notes

Reaction equation

HRID 1076123 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:15])(=O)=O.Cl>C1C=CC=CC=1>[C:1]([CH:5]1[CH2:6][CH2:7][C:8](=[O:11])[CH:9]([Cl:15])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73924-tert-ButylcyclohexanoneHCID 24648Sulfuryl chloride

Product 1

HCID 1400994-tert-Butyl-2-chlorocyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The compound 4-t-butylcyclohexanone, 154.3 grams, is dissolved in one 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 presssure to yield 167.6 grams of crude 4-t-butyl-2-chlorocyclohexanone.

Workup

  1. additionis added
  2. temperatureThe mixture is heated
  3. temperatureThe reaction mixture is slowly heated to its
  4. temperaturereflux temperature
  5. customThe solvent is removed in vacuo
  6. dissolutionthe residue dissolved in a small amount of heptane
  7. customthe eluate removed by evaporation under reduced presssure

Sources & evidence

ORD record
ord-c466c34fc346432eb23d1422ccc8a242
Source dataset
uspto-grants-1976_05
Patent number
US03954981

Reaction notes

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