2-Propenoic acid, 3-(4-formylphenyl)- → 3-(4-Formylphenyl)propanoic acid

HRID 964431Notes

Reaction equation

HRID 964431 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].C(C1C=CC(C(C)C(O)=O)=CC=1)=O>CO.[Pt]=O>[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 2

HCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 102196632-(4-Formylphenyl)propionic acid

Product 1

HCID 198252413-(4-Formylphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 253 mg (1.44 mmol) of 4-formylcinnamic acid and 32.61 mg of platinum oxide in 10 mL of methanol is stirred overnight at room temperature under an atmosphere of hydrogen supplied by a balloon. The mixture is filtered through celite and concentrated in vacuo. The residue is dissolved in 0.1N sodium hydroxide solution and washed with ether. The aqueous layer is then acidified and the product is extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent is removed in vacuo to afford an inseparable mixture of 4-formylphenylpropanoic acid and other reduction products. The mixture is utilized in the next reaction without characterization or further purification.

Workup

  1. filtrationThe mixture is filtered through celite and
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in 0.1N sodium hydroxide solution
  4. washwashed with ether
  5. extractionthe product is extracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent is removed in vacuo
  9. customto afford
  10. customThe mixture is utilized in the next reaction without characterization or further purification

Sources & evidence

ORD record
ord-05eba7feaaec488e9335ca24f5a93274
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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