1-(3-Allyl-2-hydroxyphenyl)ethanone → 1-{2-Hydroxy-3-[(1E)-prop-1-en-1-yl]phenyl}ethanone

HRID 557388Notes

Reaction equation

[CH2:1]([C:4]1[C:5]([OH:13])=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]>C1(C)C=CC=CC=1.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl>[OH:13][C:5]1[C:4](/[CH:1]=[CH:2]/[CH3:3])=[CH:9][CH:8]=[CH:7][C:6]=1[C:10](=[O:12])[CH3:11]

Participants

Conditions

Temperature: 120 °C

Procedure

40 g (227 mmol) of 1-(3-allyl-2-hydroxyphenyl)ethanone are dissolved in 120 ml of toluene, and 2.17 g (5.6 mmol) of bis(benzonitrile)dichloropalladium(II) are added. The reaction mixture is heated at 120° C. overnight. Cooling to room temperature is followed by filtration through kieselguhr and removal of the solvent in vacuo. 20.9 g (95% of theory) of the title compound are obtained and are reacted without further purification in the next stage.

Workup

temperatureCooling to room temperature
filtrationis followed by filtration through kieselguhr and removal of the solvent in vacuo

Sources & evidence

ORD record: ord-d8445f464364418fab96cf26abf2d8a4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058447B2

Reaction notes

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