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

HRID 1669746Notes

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-aba6792b0683487f850c723f927fcb29
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989633B2

Reaction notes

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