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

HRID 1951530Notes

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 in the next stage without further purification.

Workup

temperatureCooling to room temperature
filtrationis followed by filtration through kieselguhr
customthe solvent is removed in vacuo

Sources & evidence

ORD record: ord-35d091eca9074b05969eac49457cfc51
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404723B2

Reaction notes

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