4-Coumaric acid → 2-Propenoic acid, 3-phenyl-

HRID 22088

Reaction equation

HRID 22088 reaction equation
O[C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.C1OC1CO.B(F)(F)F.CCOCC.OCC(CO)O>CS(C)=O>[C:8]([OH:10])(=[O:9])[CH:7]=[CH:6][C:5]1[CH:4]=[CH:3][CH:2]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3224-Coumaric acidHCID 753GlycerolHCID 8000Boron trifluoride etherateHCID 11164Glycidol

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

8.719 g of p-hydroxy cinnamic acid was dissolved in 10 ml of DMSO, and 19.7 g of glycidol was added. The mixture was stirred and heated to 90° C. Catalystic amount of boron trifluoride ethyl ether was added, heating and agitation was carried out for 2 hours and then the adduct of cinnamic acid and glycerin was obtained.

Workup

  1. temperatureheating

Sources & evidence

ORD record
ord-12a47bbc2fa647d09b787ad23f92c3fb
Source dataset
uspto-grants-1995_06
Patent number
US05426210

Linked notes

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