Toluene → 3,3-Dimethyl-1-(4-methylphenyl)butan-1-one

HRID 911584Notes

Reaction equation

HRID 911584 reaction equation
[C:1]([CH2:5][C:6](Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:2][C:1]([CH3:4])([CH3:3])[CH2:5][C:6]([C:16]1[CH:17]=[CH:18][C:13]([CH3:19])=[CH:14][CH:15]=1)=[O:7]

Participants

4

Reactant 3

HCID 1140TolueneHCID 815143,3-Dimethylbutanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178606563,3-Dimethyl-1-(4-methylphenyl)butan-1-oneYield 100%

Procedure

Add slowly tert-butylacetyl chloride (2 g, 14.858 mmol) to an ice-cold stirred solution of aluminum trichloride (2.972 g, 22.28 mmol) in anhydrous toluene (40 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 (2.82 g, 100%) that was used without any further purification. GC-MS m/z: 190 (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-3a95ed2cbf4948cf9d2da5aff30ba757
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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