Phenol → Phenol

HRID 968980Notes

Reaction equation

HRID 968980 reaction equation
F[B-](F)(F)F.[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O[CH2:17][CH:18]=[CH2:19])(=O)C>C1(C)C=CC=CC=1>[CH2:19]([O:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:18]=[CH2:17].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11584Allyl acetateHCID 26255Tetrafluoroborate

Product 2

HCID 996PhenolHCID 74458Allyl phenyl ether

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of bis(1,5-cyclooctadiene)iridium tetrafluoroborate [Ir(cod)2]+BF4− (0.01 mmol) and toluene (1.0 ml) was treated with phenol (1 mmol) and allyl acetate (5 mmol) with stirring at 100° C. The reaction mixtures after 5 hours and after 15 hours of the reaction were analyzed by gas chromatography. In the reaction mixture after 5 hours, phenyl allyl ether was formed in a yield of 21% with a conversion from phenol of 23%. In the reaction mixture after 15 hours, phenyl allyl ether was formed in a yield of 51% with a conversion from phenol of 51%.

Workup

  1. waitIn the reaction mixture after 5 hours

Sources & evidence

ORD record
ord-64c182f7ea934e3da996f9bcfbb77e07
Source dataset
uspto-grants-2007_12
Patent number
US07304184B2

Reaction notes

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