Toluene → 4-Chloro-4'-methylbutyrophenone

HRID 1708416Notes

Reaction equation

HRID 1708416 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:7][C:1]1[CH:6]=[CH:5][C:4]([C:12](=[O:13])[CH2:11][CH2:10][CH2:9][Cl:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 987454-Chloro-4'-methylbutyrophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

53 ml of toluene and 70.5 g of 4-chlorobutyryl chloride are dissolved in 100 ml of dichloromethane, and the solution is added at 10° C. to a suspension of 74 g of aluminium chloride in 200 ml of dichloromethane. The temperature is then allowed to rise for a quarter of an hour and the mixture is treated with ice-cold water. The organic phase is dried over magnesium sulphate and evaporated under vacuum to give 96.9 g of 4'-methyl-4-chlorobutyrophenone in the form of an oil, which is used without further purification for the next step.

Workup

  1. waitto rise for a quarter of an hour
  2. additionthe mixture is treated with ice-cold water
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-af7b2226261a4299b81d505639904934
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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