Toluene → 4-Chloro-4'-methylbutyrophenone

HRID 1982525Notes

Reaction equation

HRID 1982525 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-]>C(=S)=S>[Cl:8][CH2:9][CH2:10][CH2:11][C:12]([C:4]1[CH:5]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=1)=[O:13]

Participants

5

Reactant 3

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

Product 1

HCID 987454-Chloro-4'-methylbutyrophenone

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 100 g (1.1 mole) of toluene and 146 ml (1.3 mole) of 4-chlorobutyryl chloride in 470 ml of carbon disulfide at 10° C. under N2, is added in portions, 180 g (1.4 mole) of aluminum chloride. Stir 1 hr. at 0° C., then discontinue the stirring and allow the reaction mixture to settle for 1/2 hr. Decant the top carbon disulfide layer and pour the lower layer into concentrated HCl/ice. Extract with two 600 ml portions of methylene chloride. The combined extracts are washed with 1 L of 10% potassium bicarbonate, dried over sodium sulfate and concentrated in vacuo to provide the title compound.

Workup

  1. customat 0° C.
  2. waitto settle for 1/2 hr
  3. customDecant the top carbon disulfide layer
  4. additionpour the lower layer into concentrated HCl/ice
  5. extractionExtract with two 600 ml portions of methylene chloride
  6. washThe combined extracts are washed with 1 L of 10% potassium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-786a258482524b459de8cc623dbfa395
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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