Benzyl Alcohol → Benzaldehyde

HRID 1276840Notes

Reaction equation

HRID 1276840 reaction equation
C1(C=CC(O)=CC=1)O.C(=O)([O-])[O-].[K+].[K+].FC(C1C=CC=CC=1)(F)F.[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 785HydroquinoneHCID 7368(Trifluoromethyl)benzeneHCID 11430Potassium Carbonate

Product 2

HCID 240BenzaldehydeHCID 244Benzyl Alcohol

Procedure

To a mixture of 0.1 millimole of Ru(PPh3)3Cl2 [dichlorotris(triphenylphosphine)ruthenium(II)], 0.1 millimole of hydroquinone, 0.03 millimole of potassium carbonate and 6 ml of trifluoromethylbenzene was added 1 millimole of benzyl alcohol, and the resultant mixture was stirred under oxygen atmosphere (1 atm) at 50° C. for 15 hours. The products were subjected to chromatography on silica gel (eluent: hexane/ethyl acetate=10/1) for the isolation to give benzaldehyde in a conversion rate of benzyl alcohol of 80% (yield 80%).

Sources & evidence

ORD record
ord-1ae7f5aaee2642589779883d6595d396
Source dataset
uspto-grants-2000_12
Patent number
US06166264

Reaction notes

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