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

HRID 1190945Notes

Reaction equation

HRID 1190945 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:10])[CH2:6][CH:7]([CH3:9])[CH3:8].O.[C:13]1([CH3:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH3:8][CH:7]([CH3:9])[CH2:6][C:5]([C:16]1[CH:17]=[CH:18][C:13]([CH3:19])=[CH:14][CH:15]=1)=[O:10]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 125064723-Methyl-1-(4-methylphenyl)butan-1-oneYield 97%

Procedure

Portionwise add aluminum trichloride (3.35 g, 25 mmol) to a solution of isovaleryl chloride (2 mL, 16.4 mmol) in anhydrous toluene (50 mL) at 0° C. Warm to room temperature and stir 12 h. Cool to 0° C. and slowly add cold water (500 mL). Extract with EtOAc, wash the organic phase with brine, dry over Na2SO4 and concentrate in vacuo to obtain the desired intermediate (2.8 g, 97%) as an orange oil suitable for use without additional purification. MS (APCI+) m/z: 176 (M+).

Workup

  1. customat 0° C
  2. temperatureCool to 0° C.
  3. extractionExtract with EtOAc
  4. washwash the organic phase with brine
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-79bb30e5a361426bb5134cb3c562e4c0
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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