Ethyl Acetate → 149747-03-5

HRID 922279Notes

Reaction equation

HRID 922279 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1/[CH:23]=[CH:24]/[C:25]([O:27][CH2:28][CH3:29])=[O:26])C1C=CC=CC=1.C(OCC)(=O)C>[OH-].[Pd+2].[OH-].CO>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 10548316HCID 10548316, compound

Product 1

HCID 44423246149747-03-5Yield 96.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a 500 mL parr shaker flask was charged with ethyl (2E)-3-[2,4-bis(benzyloxy)phenyl]prop-2-enoate (2.3 g, 5.92 mmol), ethyl acetate (10 mL) and methanol (10 mL). To the reaction mixture was added palladium hydroxide (20%) and kept for hydrogenation at 50 psi for 2 h. After completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with ethyl acetate (25 mL) and concentrated to distill off the solvent. The product was obtained as brown solid (1.2 g, yield: 96.8%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. washwashed thoroughly with ethyl acetate (25 mL)
  4. concentrationconcentrated
  5. distillationto distill off the solvent

Sources & evidence

ORD record
ord-8a0f0dc061cc4e21915f5f287e8239f1
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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