Alpha-Cyano-4-Hydroxycinnamic Acid → 2-Cyano-3-(4-hydroxyphenyl)propanoic acid

HRID 922185Notes

Reaction equation

HRID 922185 reaction equation
[C:1]([C:3](=[CH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5])#[N:2]>C(OCC)(=O)C>[C:1]([CH:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)[C:4]([OH:6])=[O:5])#[N:2]

Participants

3

Reactant 1

HCID 2102Alpha-Cyano-4-Hydroxycinnamic Acid

Product 1

HCID 193792182-Cyano-3-(4-hydroxyphenyl)propanoic acidYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL par shaker flask was charged 2-cyano-3-(4-hydroxy-phenyl)-acrylic acid (0.5 g, 2.6 mmol) in ethyl acetate (10 mL) and the solution was purged with nitrogen for 10 minutes. Then 10% palladium on carbon (0.07 g) was added under nitrogen atmosphere. After addition, the mixture was hydrogenated at 30 psi for 3 days. After completion of the reaction (monitored by TLC), the RM was filtered through celite bed and the residue was washed thoroughly with methanol (15 mL). After filtration, the filtrate was concentrated to distill off the solvent and dried under vacuum. The product was obtained as yellow liquid 0.5 g, yield: 98.9%): MS (ESI, 120 eV): m/z=192.1 (M+H)+; 1H NMR (300 MHz, DMSO-d6): δ 7.07-7.10 (d, 2H), 6.70-6.72 (d, 2H), 4.17-4.21 (t, 1H), 2.92-3.09 (m, 2H).

Workup

  1. customthe solution was purged with nitrogen for 10 minutes
  2. additionThen 10% palladium on carbon (0.07 g) was added under nitrogen atmosphere
  3. additionAfter addition
  4. customAfter completion of the reaction (monitored by TLC)
  5. filtrationthe RM was filtered through celite bed
  6. washthe residue was washed thoroughly with methanol (15 mL)
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. distillationto distill off the solvent
  10. customdried under vacuum

Sources & evidence

ORD record
ord-756c38e0649b41e7b56a08b550d1c9cd
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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