Hydrogen Bromide → 2-Propenoic acid, 3-phenyl-, methyl ester

HRID 1658902Notes

Reaction equation

HRID 1658902 reaction equation
[C:1]1(P([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH2:21]([OH:24])[CH:22]=[CH2:23].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH2:27]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:25]([O:29][CH3:30])(=[O:28])/[CH:26]=[CH:27]/[CH:2]=[CH:1]/[CH3:6].[C:14]([O:24][CH2:21][CH:22]=[CH2:23])(=[O:28])/[CH:19]=[CH:18]/[CH:17]=[CH:16]/[CH3:15].[C:25]([O:29][CH3:30])(=[O:28])[CH:26]=[CH:27][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 7858Allyl AlcoholHCID 11776Triphenylphosphine

Product 3

HCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 5323650Methyl sorbateHCID 6435833Allyl sorbate

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
135 °C

Procedure

Quantities of 5 millimoles palladium acetate, 20 millimoles triphenyl phosphine, 5 millimoles of hydrogen bromide, 600 millimoles allyl alcohol, and 600 millimoles methyl acrylate are introduced into a reaction chamber and heated to 135°C for 20 hours. The final reaction solution produced 15% by weight methyl sorbate, allyl sorbate, and traces of methyl cinnamate.

Workup

  1. customThe final reaction solution

Sources & evidence

ORD record
ord-b7841dbc5b3f4c0d944dbee568bac915
Source dataset
uspto-grants-1976_06
Patent number
US03966798

Reaction notes

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