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

HRID 328172Notes

Reaction equation

HRID 328172 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 15 minutes with vigorous stirring and cooling in an ice-bath. Cyclohexylbenzene (481 g.; 3.0 moles) is added dropwise over a period of 3 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-bfd9fc9767ed4168b6b660882cce32be
Source dataset
uspto-grants-1977_04
Patent number
US04016214

Reaction notes

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