Hydrochloric Acid → 6-Bromo-1-(4-methylphenyl)-1-hexanone

HRID 344252Notes

Reaction equation

HRID 344252 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11](Cl)=[O:12].Cl.[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[Br:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([C:18]1[CH:19]=[CH:20][C:15]([CH3:21])=[CH:16][CH:17]=1)=[O:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 539283736-Bromo-1-(4-methylphenyl)-1-hexanone

Procedure

Aluminum chloride (1.3 g) was added to a solution of 6-bromohexanoyl chloride (2 g) in toluene (20 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hr. Ice water and conc. hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was evaporated under reduced pressure to give 2.76 g of 6-bromo-1-(4-methylphenyl)-1-hexanone.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-609b1122e0954e50b472a6e10989a113
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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