Toluene → 4-Methylbenzophenone

HRID 1935612Notes

Reaction equation

HRID 1935612 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5](Cl)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH3:20][C:14]1[CH:19]=[CH:18][C:17]([C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:12])=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 86524-MethylbenzophenoneYield 73.5%

Conditions

Temperature
30 °C

Procedure

To the mixture of anhydrous AlCl3 (85 g, 0.64 mole) with dried toluene (90 mL) was added benzoyl chloride (50 mL, 0.43 mole) dropwise at 10±2° C. The mixture was warmed to 30±2° C. and stirred for 12 hours, and then heated to 100±5° C. and stirred for another 2 hr before it was cooled and added into ice water (200 mL) to terminate the reaction. The organic layer was separated and washed successively with water, 5% sodium carbonate and then water again till neutralized. The organic layer was dried over anhydrous magnesium sulfate and evaporated for solvent removal. The residue was recrystallized from n-hexane to obtain 62.1 g 4-methylbenzophenone in a yield 73.5%. mp: 55-57° C.

Workup

  1. temperatureheated to 100±5° C.
  2. stirringstirred for another 2 hr before it
  3. temperaturewas cooled
  4. customto terminate
  5. customthe reaction
  6. customThe organic layer was separated
  7. washwashed successively with water, 5% sodium carbonate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customevaporated for solvent removal
  10. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-b3e08b0a6c2a4e169115bdda8a4a4a53
Source dataset
uspto-grants-2002_05
Patent number
US06387942B2

Reaction notes

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