Toluene → 7-Phenyl-1-tetralone

HRID 565833

Reaction equation

HRID 565833 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:12]1(OB([O-])[O-])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>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(O)C>[C:12]1([C:8]2[CH:9]=[C:10]3[C:5]([CH2:4][CH2:3][CH2:2][C:1]3=[O:11])=[CH:6][CH:7]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 107241-TetraloneHCID 11430Potassium CarbonateHCID 19793864Phenylborate

Product 1

HCID 37782357-Phenyl-1-tetraloneYield 78.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 7- (trifluoromethanesulfoxy) -1-tetralone (23.3 g), phenylborate (11.8 g), potassiumcarbonate (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-3d159f5def2a4171894e1b3528ca33ed
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Linked notes

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