P-Toluic Acid → Methanone, (2,5-dimethylphenyl)(4-methylphenyl)-

HRID 2248956Notes

Reaction equation

HRID 2248956 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[CH:6][CH:7]=1.FC(F)(F)S(O)(=O)=O>CC1C=CC(C)=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][C:7]=1[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 7470P-Toluic AcidHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 4380648Methanone, (2,5-dimethylphenyl)(4-methylphenyl)-Yield 135%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

A mixture of p-toluic acid (22.2 g, 0.163 mole), p-xylene (100 mL), and trifluoromethanesulfonic acid (5 mL; 0.056 mole) was heated at reflux for 21 hours in a 300 mL flask equipped with a Dean-Stark trap, after which time 3 mL of water had been collected in the trap. The progress of the reaction was measured by gas chromatography as well as by the amount of water collected. After 6 hours, 22% of starting material had been converted to 2,5,4'-trimethylbenzophenone. The mixture was extracted with water, with 5% aqueous sodium hydroxide solution, and again with water. Evaporation of the organic layer gave 24 g (0.11 mole) of 2,5,4'-trimethylbenzophenone, 66% of theory.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 hours in a 300 mL flask
  3. customequipped with a Dean-Stark trap
  4. customafter which time 3 mL of water had been collected in the trap
  5. customcollected
  6. extractionThe mixture was extracted with water, with 5% aqueous sodium hydroxide solution
  7. customEvaporation of the organic layer

Sources & evidence

ORD record
ord-7587c50ac96c46e0be0fe193f8923cbb
Source dataset
uspto-grants-1991_08
Patent number
US05041616

Reaction notes

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