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

HRID 2090183Notes

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 the solvent is removed 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
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-3bf1d832bfcf4008ba3035b0ba5e0ad0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436180B2

Reaction notes

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