4-Formylcinnamic acid dimethyl acetal → 3-(4-Formylphenyl)propanoic acid

HRID 328921Notes

Reaction equation

HRID 328921 reaction equation
C[O:2][C:3](OC)([OH:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1>O1CCOCC1.[Pd]>[CH:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:14])=[O:2])=[CH:7][CH:8]=1)=[O:13]

Participants

4

Reactant 1

HCID 865896714-Formylcinnamic acid dimethyl acetal

Product 1

HCID 198252413-(4-Formylphenyl)propanoic acidYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 16.7 g of 4-formylcinnamic acid dimethyl acetal in 200 ml of dioxane was hydrogenated in the presence of 1 g of 5% palladium-on-carbon at room temperature and atmospheric pressure. After about 61/2 hrs., the theoretical volume of hydrogen was consumed and the uptake ceased. The reaction mixture was filtered through Celite and the filter cake was washed with 300 ml of dioxane. The filtrate was concentrated to a final volume of 200 ml, 200 ml of 1N hydrochloride acid was added, the solution was stirred at room temperature for 4 hrs. and then evaporated to dryness. The residue was dissolved in 700 ml of methylene chloride, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to a final volume of 100 ml and the solution was allowed to stand at 0° for 16 hrs. The precipitate was collected, washed with 1:1 methylene chloride-petroleum ether and dried at 55° for 4 hrs. under vacuum to give 10.9 g (81%) of 4-formyldihydrocinnamic acid as colorless crystals, m.p. 134°-138°.

Workup

  1. custom2 hrs
  2. custom, the theoretical volume of hydrogen was consumed
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filter cake was washed with 300 ml of dioxane
  5. concentrationThe filtrate was concentrated to a final volume of 200 ml, 200 ml of 1N hydrochloride acid
  6. additionwas added
  7. customand then evaporated to dryness
  8. dissolutionThe residue was dissolved in 700 ml of methylene chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated to a final volume of 100 ml
  12. waitto stand at 0° for 16 hrs
  13. customThe precipitate was collected
  14. washwashed with 1:1 methylene chloride-petroleum ether
  15. customdried at 55° for 4 hrs

Sources & evidence

ORD record
ord-72bdb07272fe40b3913a5748ce95691c
Source dataset
uspto-grants-1977_04
Patent number
US04018884

Reaction notes

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