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

HRID 439337Notes

Reaction equation

HRID 439337 reaction equation
[Al+3].[Cl-].[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 AlCl3 (40.0 g, 0.3 mole) in benzene (90 mL) maintained at 10° C. under argon was added dropwise mesityl oxide (0.2 mole, 19.63 g). 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 H2O, saturated NaHCO3 solution, saturated NaCl solution and dried over Na2SO4. The solvent was recovered under vacuum and the crude product (31.6 g) was vacuum distilled (b.p.=107° C. @ 3.0 mmHg) to obtain 24.5 g (69%) of the title A compound as a colorless oil. MS: (M+H)+ @ 177.

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 H2O, saturated NaHCO3 solution, saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was recovered under vacuum
  8. distillationdistilled (b.p.=107° C. @ 3.0 mmHg)

Sources & evidence

ORD record
ord-31e5379c721746c5804a6d28fb15f917
Source dataset
uspto-grants-1996_05
Patent number
US05514690

Reaction notes

Loading…