1-Phenyl-1-propanone → 1,2-Diphenylpropan-1-one

HRID 1421113Notes

Reaction equation

HRID 1421113 reaction equation
CC([O-])(C)C.[Na+].Cl[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])[CH2:15][CH3:16]>C1COCC1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]1([C:14](=[O:17])[CH:15]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 7964ChlorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 2385181,2-Diphenylpropan-1-oneYield 97%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Pd(OAc)2 (4.5 mg, 0.020 mmol), Tri-cyclohexyphosphine (5.6 mg, 0.020 mmol) and NaOtBu (144 mg, 1.50 mmol) were suspended in 1 mL of THF in a screw-capped vial. The vial was sealed with a cap containing a PTFE septum and removed from the dry box. Chlorobenzene (113 mg, 1.00 mmol) and propiophenone (144 mg, 1.10 mmol) were added to the reaction mixture by syringe. The reaction mixture was stirred at 50° C. and monitored by GC analysis. The crude reaction was diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/EtOAc=95/5) to give 204 mg (97%) of 1,2-Diphenyl-1-propanone.

Workup

  1. customThe vial was sealed with a cap
  2. customremoved from the dry box
  3. customThe crude reaction
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (hexane/EtOAc=95/5)

Sources & evidence

ORD record
ord-bf77fc1bd97144549df1b8c1b512c281
Source dataset
uspto-grants-2000_06
Patent number
US06072073

Reaction notes

Loading…