Benzene → 2-Pentanone, 4-methyl-4-phenyl-

HRID 1609694Notes

Reaction equation

HRID 1609694 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[O:5]=[C:6]([CH:8]=[C:9]([CH3:11])[CH3:10])[CH3:7].[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:10][C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH2:8][C:6](=[O:5])[CH3:7]

Participants

4

Reactant 3

HCID 241BenzeneHCID 8858Mesityl oxideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 818982-Pentanone, 4-methyl-4-phenyl-

Procedure

To a slurry of aluminum chloride (40.0 g, 0.3 mole) in benzene (90 ml) maintained at 10° C. under argon was added dropwise mesityl oxide (19.63 g, 0.2 mole). Upon completion of the addition the reaction was stirred at room temperature for 1.5 hours. The reaction mixture was poured onto ice/10% HCl (350 g). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 ml). The combined organics were washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution and dried over sodium sulfate. The solvent was evaporated under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. at 3.0 mmHg) to obtain 24.5 g of the title A compound as a colorless oil. 1H NMR (CDCl3) δ 7.38-7.19 (m, 5H), 2.74 (s, 2H), 1.80 (s, 3H), 1.43 (s, 6H). 13C NMR (CDCl 3) δ 207.94, 148.16, 128.26, 125.95, 125.46, 56.96, 37.29, 31.76, 28.88.

Workup

  1. additionUpon completion of the addition the reaction
  2. additionThe reaction mixture was poured onto ice/10% HCl (350 g)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (100 ml)
  5. washThe combined organics were washed with distilled water, saturated sodium hydrogen carbonate solution, saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under vacuum
  8. distillationdistilled (b.p.=107° C. at 3.0 mmHg)

Sources & evidence

ORD record
ord-5c95f8d9d83e46738346577bec641240
Source dataset
uspto-grants-1995_03
Patent number
US05401848

Reaction notes

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