1,3-Cyclohexanedione, 5-phenyl- → [1,1′-Biphenyl]-3,5-diol

HRID 488676Notes

Reaction equation

HRID 488676 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][C:9](=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.[Pd]>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([OH:13])[CH:12]=1

Participants

5

Reactant 1

HCID 5689621,3-Cyclohexanedione, 5-phenyl-

Product 1

HCID 604248[1,1′-Biphenyl]-3,5-diol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
230 °C

Procedure

A mixture of 5-phenyl-1,3-cyclohexanedione (2.5 g, 13 mM) and 10% Pd/C (0.5 g) in phenyl ether (30 mL) was heated to 230° C. over 30 minutes and held at 230° C. for 2.5 hours. The reaction was cooled, taken up in CH2Cl2 and filtered through Dicalite. The filtrate was concentrated and the residue purified by chromatography (CH2Cl2, then 5-10% EtOAc/CH2Cl2) to give the desired product.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through Dicalite
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by chromatography (CH2Cl2

Sources & evidence

ORD record
ord-e502539a783544919ad7a7c8591cf916
Source dataset
uspto-grants-2005_12
Patent number
US06972340B2

Reaction notes

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