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

HRID 1951364Notes

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-dff45ee288c141d6a0bf0d80525e0384
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404709B2

Reaction notes

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