Toluene → 3-Methyl-1-(4-methylphenyl)butan-1-one

HRID 911706Notes

Reaction equation

HRID 911706 reaction equation
[C:1](Cl)(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:12]1([CH3:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:4][CH:3]([CH3:5])[CH2:2][C:1]([C:15]1[CH:16]=[CH:17][C:12]([CH3:18])=[CH:13][CH:14]=1)=[O:6]

Participants

4

Reactant 3

HCID 1140TolueneHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125064723-Methyl-1-(4-methylphenyl)butan-1-oneYield 100%

Procedure

Add slowly isovaleryl chloride (3.0 g, 24.88 mmol) to an ice-cold stirred solution of aluminum trichloride (4.976 g, 37.32 mmol) in anhydrous toluene (60 mL). Stir the reaction mixture at ambient temperature overnight. Add slowly ice-cold water and extract the mixture twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give the desired intermediate (4.38 g, 100%) that was used without any further purification. GC-MS m/z: 176 (M+).

Workup

  1. additionAdd slowly ice-cold water
  2. extractionextract the mixture twice with EtOAc
  3. dry with materialDry the combined organic extracts over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d580b12a7af14e8a8e69c23bce00f1ef
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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