Benzene → Cyclohexyl phenyl ketone

HRID 279142

Reaction equation

HRID 279142 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Al+3].[Cl-].[Cl-].[Cl-].[CH:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12837Cyclohexyl phenyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2 °C

Procedure

A solution of cyclohexanecarbonyl chloride (9.1 ml) in CH2Cl2 (25 ml) was added slowly under nitrogen atmosphere at 0-4° C. to a stirred mixture of AlCl3 (9.1 g), CH2Cl2 (25 ml) and benzene (50 ml). The resulting mixture was stirred for 1 hour at 0-4° C. and 12 hours at the room temperature. The mixture was poured into ice-water (200 ml, contains 1 ml of concentrated HCl) and stirred for 5 minutes. The phases were separated and the aqueous phase was washed with CH2CO2 (2×20 ml). The organic phases were combined and extracted with water (2×20 ml), 2.5% NaOH solution (2×30 ml) and water (2×20 ml). The organic phase was dried over Na2SO4 and evaporated. Yield was 12.0 g.

Workup

  1. stirringstirred for 5 minutes
  2. customThe phases were separated
  3. washthe aqueous phase was washed with CH2CO2 (2×20 ml)
  4. extractionextracted with water (2×20 ml), 2.5% NaOH solution (2×30 ml) and water (2×20 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-02badd5f167345fb8edeafd29fdabb7c
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Linked notes

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