Hydrochloric Acid → 1-(4-Cyclohexylphenyl)ethan-1-one

HRID 1606277Notes

Reaction equation

HRID 1606277 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Cl>C(Cl)(Cl)(Cl)Cl>[CH:15]1([C:9]2[CH:10]=[CH:11][C:12]([C:5](=[O:7])[CH3:6])=[CH:13][CH:14]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 13229CyclohexylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 877151-(4-Cyclohexylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of anhydrous aluminum chloride (467 g,; 3.5 moles) in carbon tetrachloride (2 l.) is added acetyl chloride (275 g.; 249 cc., 3.5 moles) during fifteen minutes with vigorous stirring and cooling in an ice-bath. Cyclohexylbenzene (481 g,; 3.0 moles) is added dropwise over a period of three hours, keeping the temperature below 5°. After addition is complete, the product is stirred for another hour before hydrolyzing by pouring into ice and hydrochloric acid with stirring. The organic phase is washed with successive portions of dilute hydrochloric acid, sodium carbonate, and water, and distilled to give p-cyclohexylacetophenone, (b.p. 88°-95.5°/0.05 mm.)

Workup

  1. temperaturecooling in an ice-bath
  2. customthe temperature below 5°
  3. additionAfter addition
  4. stirringthe product is stirred for another hour before hydrolyzing
  5. stirringwith stirring
  6. washThe organic phase is washed with successive portions of dilute hydrochloric acid, sodium carbonate, and water
  7. distillationdistilled

Sources & evidence

ORD record
ord-12a5e5f6883246f6b51a0cecf33969fc
Source dataset
uspto-grants-1976_04
Patent number
US03952067

Reaction notes

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