1-Phenyl-1-propanone → HCID 22558559, compound

HRID 984745Notes

Reaction equation

HRID 984745 reaction equation
[CH3:1]C(C)([O-])C.[Na+].BrC1[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=1.[C:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH2:17][CH3:18]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:15][C:10]1[CH:9]=[C:18]([CH:17]([CH3:1])[C:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:13]=[C:12]([CH3:14])[CH:11]=1

Participants

6

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 23676156Sodium t-butoxide

Product 1

HCID 22558559HCID 22558559, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A dry Schlenk tube was charged with Pd2 (DBA)3 (4.6 mg, 0.005 mmol) and sodium tert-butoxide (125 mg, 1.3 mmol). The tube was then evacuated and filled with argon. Toluene (1 mL), 5-bromo-m-xylene (185 mg, 0.136 mL, 1.0 mmol) and propiophenone (161 mg, 0.160 mL, 1.2 mmol) were sequentially added with a syringe, and the tube was sealed and heated in an, oil bath at 80° C. for 12 h. The mixture was cooled, and partitioned between ether and water. The aqueous layer was extracted twice with ether, and the combined organics were dried over Na2SO4, filtered and concentrated. Chromatography on silica gel, eluting first with hexane, then 4:1 toluene:hexane, gave 0.185 g (79%) of α-(3,5-dimethylphenyl)propiophenone, a clear oil. 1H NMR (CDCl3, 300 MHz) δ 7.96 (m, 2H); 7.48 (m, 1H); 7.38 (m, 214); 6.89 (s, 2H); 6.83 (s, 2H); 4.60 (q, 1H, J=6.9 Hz); 2.26 (s, 6H); 1.50 (d, 3H, J=6.9 Hz).

Workup

  1. customThe tube was then evacuated
  2. additionfilled with argon
  3. customthe tube was sealed
  4. temperatureThe mixture was cooled
  5. custompartitioned between ether and water
  6. extractionThe aqueous layer was extracted twice with ether
  7. dry with materialthe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washChromatography on silica gel, eluting first with hexane

Sources & evidence

ORD record
ord-de9683af75774e3f8ca2027e2e8ac5b7
Source dataset
uspto-grants-2005_03
Patent number
US06867310B1

Reaction notes

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