Acetyl chloride → 4-Acetyl-1-(4-pentylphenyl)-cyclohexane

HRID 66049Notes

Reaction equation

HRID 66049 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1>C(=S)=S>[C:5]([CH:9]1[CH2:14][CH2:13][CH:12]([C:9]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][CH2:14][CH3:13])=[CH:11][CH:10]=2)[CH2:11][CH2:10]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8079CyclohexeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 152199654-Acetyl-1-(4-pentylphenyl)-cyclohexane

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a suspension of 66.6 g. of anhydrous aluminum chloride in 200 ml. of carbon disulphide there are added at -15° C., with stirring, 39 g. of acetyl chloride and thereafter 41 g. of cyclohexene. The reaction mixture is stirred for 30 minutes at -15° C. and then the upper carbon disulphide layer is removed and replaced by 400 ml. of n-pentylbenzene. After the addition of a further 33 g. of aluminum chloride, while stirring, the reaction mixture is warmed up to ambient temperature and further stirred until the evolution of hydrogen chloride ceases. Thereafter, the reaction mixture is poured onto ice water, the separated aluminum hydroxide is brought into solution with hydrochloric acid and the organic phase is separated off, dried and distilled. After stripping off excess n-pentylbenzene, the 4-acetyl-1-(4-pentylphenyl)-cyclohexane thus obtained is distilled off under reduced pressure; yield 48 g.

Workup

  1. additionTo a suspension of 66.6 g
  2. stirringThe reaction mixture is stirred for 30 minutes at -15° C.
  3. customthe upper carbon disulphide layer is removed
  4. additionAfter the addition of a further 33 g
  5. stirringof aluminum chloride, while stirring
  6. stirringfurther stirred until the evolution of hydrogen chloride ceases
  7. additionThereafter, the reaction mixture is poured onto ice water
  8. customthe organic phase is separated off
  9. customdried
  10. distillationdistilled

Sources & evidence

ORD record
ord-76f0ce42955746c382924ac2cc7d580a
Source dataset
uspto-grants-1978_12
Patent number
US04130502

Reaction notes

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