Toluene → p-METHYLACETOPHENONE

HRID 500748Notes

Reaction equation

HRID 500748 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(=S)=S>[C:5]1([CH3:11])[CH:10]=[CH:9][C:8]([C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8500p-METHYLACETOPHENONEYield 67,275,272%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Anhydrous aluminum chloride (89.6 g, 0.67 mol) was added to a solution of toluene (28.5 g, 0.3 μmol) in 120 mL of dry carbon disulfide. The mixture was heated to reflux and acetic anhydride (24.5 g, 0.24 mol) was added over one hour. Heating was continued for an additional hour. The solvent was removed by distillation. The reaction mixture was cooled and slowly poured into a well-stirred mixture of ice and hydrochloric acid. The mixture was extracted several times with ether. The combined extracts were washed with water and 10% sodium hydroxide, dried over calcium chloride, filtered, and the solvent was removed. Distillation gave the desired product 1-p-tolyl-ethanone (27.08 g). 1H NMR (300 MHz, DMSO-d6) δ 2.36 (s, 3H), 2.50 (s, 3H), 7.32 (d, 2H), 7.85 (d, 2H); EI-MS (M+): 134.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureHeating
  4. waitwas continued for an additional hour
  5. customThe solvent was removed by distillation
  6. temperatureThe reaction mixture was cooled
  7. additionslowly poured into a well-stirred mixture of ice and hydrochloric acid
  8. extractionThe mixture was extracted several times with ether
  9. washThe combined extracts were washed with water and 10% sodium hydroxide
  10. dry with materialdried over calcium chloride
  11. filtrationfiltered
  12. customthe solvent was removed
  13. distillationDistillation

Sources & evidence

ORD record
ord-60ac21979dd54509bc49548bee357e38
Source dataset
uspto-grants-2010_08
Patent number
US07772248B2

Reaction notes

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