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

HRID 22094

Reaction equation

HRID 22094 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>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

3

Reactant 1

HCID 3224-Coumaric acid

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

2.8 g of p-hydroxy cinnamic acid was dissolved in 3 ml of DMSO, and 10 mg of sodium hydride of which the oil was washed by hexane was added. The mixture was stirred and heated to 90° C. under a flow of N2 gas. 5.0 g of glycidol was added gradually, heating and agitation were carried out for 1.5 hours, neutralized by adding hydrochloric acid and then the adduct of cinnamic acid and glycerin was obtained.

Workup

  1. wash10 mg of sodium hydride of which the oil was washed by hexane
  2. additionwas added
  3. addition5.0 g of glycidol was added gradually
  4. temperatureheating
  5. additionby adding hydrochloric acid

Sources & evidence

ORD record
ord-2231e991bda54208932c1c846850f007
Source dataset
uspto-grants-1995_06
Patent number
US05426210

Linked notes

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