Ethanol → 7-Phenyl-1-tetralone

HRID 1387766Notes

Reaction equation

HRID 1387766 reaction equation
B([O-])([O-])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11](=O)([O-])[O-].[K+].[K+].[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:24](O)[CH3:25]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:17]1([C:23]2[CH:11]=[C:8]3[C:7]([CH2:6][CH2:5][CH2:4][C:3]3=[O:2])=[CH:25][CH:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 19793864Phenylborate

Product 1

HCID 37782357-Phenyl-1-tetralone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 7-(trifluoromethanesulfoxy)-1-tetralone (23.3 g), phenyl borate (11.8 g), potassium carbonate (21.9 g), toluene (500 ml), ethanol (50 ml) and water (50 ml) was stirred for 30 minutes at room temperature under argon atmosphere, and to the mixture was added tetrakis(triphenylphosphine)palladium (3.66 g). The mixture was refluxed for 20 hours and then cooled to room temperature. The organic layer was separated, washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene/hexane=1/5/5) to give 7-phenyl-1-tetralone (15.1 g) as pale brown oil.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was separated
  8. custompurified with column chromatography (ethyl acetate/toluene/hexane=1/5/5)

Sources & evidence

ORD record
ord-ac73b9f12ec049cf897a6f24d0267fa1
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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