Toluene → 1-Propanone, 2-methyl-1-(4-methylphenyl)-

HRID 223113Notes

Reaction equation

HRID 223113 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:9])[CH:6]([CH3:8])[CH3:7].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[N+](C)([O-])=O>[CH:6]([C:5]([C:14]1[CH:15]=[CH:16][C:11]([CH3:17])=[CH:12][CH:13]=1)=[O:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 5768291-Propanone, 2-methyl-1-(4-methylphenyl)-Yield 90%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent2×

Procedure

At 10° C. a solution of 75 g AlCl3 in 100 ml nitromethane is added to a mixture of 49 g isobutyroyl chloride, 50 ml nitromethane and 100 ml toluene, after which the mixture is stirred during one hour. Then the reaction mixture is poured out into ice and extracted with ether. The ether solution is washed neutral, dried and evaporated. The residue is distilled under diminished pressure to obtain p-tolyl isopropyl ketone in a yield of 90%. 11 g of this ketone, dissolved in 50 ml methanol, is added to a solution of 10 g NaBH4 in 100 ml methanol/water 1:1. The reaction mixture is stirred during one hour, after that poured out into water and extracted with ether. The solution in ether is dried on MgSO4 and evaporated. Raw 2-methyl-1-(p-tolyl)propanol-1 is obtained in a yield of 97%.

Workup

  1. additionThen the reaction mixture is poured out into ice
  2. extractionextracted with ether
  3. washThe ether solution is washed neutral
  4. customdried
  5. customevaporated
  6. distillationThe residue is distilled under diminished pressure

Sources & evidence

ORD record
ord-767d20576bda4d42ad68cf3a46d68ae4
Source dataset
uspto-grants-1982_10
Patent number
US04352748

Reaction notes

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