Toluene → HCID 57318013, compound

HRID 274247Notes

Reaction equation

HRID 274247 reaction equation
ClC[CH2:3][CH2:4][C:5](Cl)=[O:6].[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Al+3].[Cl-:16].[Cl-].[Cl-].Cl[CH2:20]Cl>>[Cl:16][CH2:3][CH2:4][C:5](=[O:6])[CH2:14][C:8]1[CH:13]=[CH:12][C:11]([CH3:20])=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6344DichloromethaneHCID 783704-Chlorobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57318013HCID 57318013, compound

Procedure

A mixture of 560 ml of 4-chlorobutyryl chloride and 550 ml of toluene is added dropwise to a suspension of 740 g of AlCl3 in 2 l of dichloromethane, the temperature being maintained at between 10° and 15° C. The reaction mixture is stirred for 30 min at room temperature and poured on to ice. After decantation, the organic phase is separated off and the aqueous phase is extracted with dichloromethane. The organic phases are combined, washed with water and then dried and concentrated under vacuum to give 994.5 g of 4-chloro-1-(4-methylphenyl)butanone in the form of an oil, which is used in the next step without further purification.

Workup

  1. temperaturethe temperature being maintained at between 10° and 15° C
  2. additionpoured on to ice
  3. customAfter decantation, the organic phase is separated off
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c97a58922405418aa9f10c5f6967f9cf
Source dataset
uspto-grants-1995_02
Patent number
US05389632

Reaction notes

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