Toluene → 4,4'-Dimethylbenzophenone

HRID 279696Notes

Reaction equation

HRID 279696 reaction equation
C([O-])(O)=O.[Na+].[C:6]1([CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]1([CH3:22])[CH:18]=[CH:17][C:16]([C:19](O)=[O:20])=[CH:15][CH:14]=1>O>[CH3:12][C:6]1[CH:11]=[CH:10][C:9]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:22])=[CH:14][CH:15]=2)=[O:20])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7470P-Toluic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 691484,4'-DimethylbenzophenoneYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The three water extracts from Example 4 (excluding the NaHCO3 extracts) were charged into a 200 mL flask along with toluene (50 mL) and para-toluic acid (1.36 g). The mixture was heated and water was removed azeotropically as in Example 3;once approximately 40 mL of water had been removed a further 50 mL toluene was added. Then, when a total of 75 mL of water had been removed, a final 25 mL toluene was added. The reflux was terminated after 18 hours. After workup (as in Example 3) the reaction gave crude 4,4′-dimethylbenzophenone (0.58 g, 28% yield), which was again practically pure by 1H NMR (M.P. 86.5-87.5° C.). Removal of water from the three water extracts recovered 3.40 g cerium (III) trifluoromethanesulfonate as a damp, off-white solid).

Workup

  1. temperatureThe mixture was heated
  2. customhad been removed a further 50 mL toluene
  3. additionwas added
  4. customThen, when a total of 75 mL of water had been removed
  5. additiona final 25 mL toluene was added
  6. customThe reflux was terminated after 18 hours

Sources & evidence

ORD record
ord-0f53e5e7cb084b198b5d3fa70fa8ed46
Source dataset
uspto-grants-2002_03
Patent number
US06362375B1

Reaction notes

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