3-Phenylprop-2-En-1-Ol → 2-Propenoic acid, 3-phenyl-

HRID 599723Notes

Reaction equation

HRID 599723 reaction equation
O=O.[CH2:3]([OH:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)([O-])[O-:14].[K+].[K+]>[Pt].O>[C:3]([OH:14])(=[O:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 977OxygenHCID 11430Potassium Carbonate

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 96.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

In an ambient pressure oxygen atmosphere, 40.3 mg of cinnamyl alcohol, 105.3 mg of the platinum catalyst obtained in Example 1 and 40.2 mg of potassium carbonate were agitated for eighteen hours at 60° C. in 3 ml of water. The aqueous layer was subsequently washed using tert-butyl methyl ether and was extracted using ethyl acetate after neutralizing the layer with a HCl solution. The ethyl acetate solution was dried using magnesium sulfate, filtered and concentrated to obtain 41.5 mg (93% yield) of cinnamic acid. The reaction equation and the analytical results of the product are shown below.

Workup

  1. washThe aqueous layer was subsequently washed
  2. extractionwas extracted
  3. dry with materialThe ethyl acetate solution was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8181723e5da3472a9ecdbf0f0398a5a4
Source dataset
uspto-grants-2011_03
Patent number
US07897817B2

Reaction notes

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