Anisole → Cyclohexyl(4-methoxyphenyl)methanone

HRID 484338Notes

Reaction equation

HRID 484338 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]1([O:16][CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[CH:1]1([C:7]([C:13]2[CH:14]=[CH:15][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 345014Cyclohexyl(4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

42.6 g (0.291 mol) of cyclohexanecarbonyl chloride and then 30 g (0.277 mol) of anisole are added dropwise at room temperature to a suspension of 44.4 g (0.33 mol) of aluminium chloride in 120 ml of dichloroethane. The reaction mixture is stirred for 1 h and allowed to stand overnight. For working up, the mixture is poured into ice-water and the aqueous phase is extracted with dichloromethane. The organic phase is washed with 1N NaOH and water, dried over sodium sulphate and concentrated in vacuo.

Workup

  1. waitto stand overnight
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. washThe organic phase is washed with 1N NaOH and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31c7b7152d684d51b1fdea4286e39ce0
Source dataset
uspto-grants-1993_07
Patent number
US05231103

Reaction notes

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