Water → HCID 10921586, compound

HRID 1156630Notes

Reaction equation

HRID 1156630 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=O)[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.[OH2:21]>ClCCl>[CH2:18]1[CH2:17][CH2:16][CH:15]([CH2:9][C:14]([C:13]2[CH:12]=[CH:11][CH:10]=[CH:6][CH:5]=2)=[O:21])[CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 13229CyclohexylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10921586HCID 10921586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

There was introduced to a 1 liter 3-neck flask under nitrogen atmosphere 41.7 g (0.312 Mol) of aluminum chloride, followed by 250 ml of dichloromethane. The mixture was cooled in an ice bath and 39.3 g (0.5 Mol) of acetyl chloride was added dropwise. This was followed by dropwise addition of 40.0 g of cyclohexylbenzene in 100 ml of dichloromethane. Fifteen minutes after addition was complete, 25 g of ice and then 25 ml of water were added to the reaction mixture, whereupon a thick white solid formed. The dichloromethane was decanted and washed with water, then three times with 30 ml of saturated saline solution, after which it was dried overnight over magnesium sulfate. After filtration, the remaining dichloromethane was evaporated, and the residue crystallized on cooling. The residue was recrystallized from petroleum ether to give 28.1 g. of product, m.p. 65°-67° C. Analysis:

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionFifteen minutes after addition
  3. customformed
  4. customThe dichloromethane was decanted
  5. washwashed with water
  6. dry with materialthree times with 30 ml of saturated saline solution, after which it was dried overnight over magnesium sulfate
  7. filtrationAfter filtration
  8. customthe remaining dichloromethane was evaporated
  9. customthe residue crystallized
  10. temperatureon cooling
  11. customThe residue was recrystallized from petroleum ether
  12. customto give 28.1 g

Sources & evidence

ORD record
ord-b82e2469e763447bbec7cf793d272d16
Source dataset
uspto-grants-1982_06
Patent number
US04336397

Reaction notes

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