(E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylate → Ethyl 3-(4-hydroxy-2 isopropoxyphenyl)propanoate

HRID 1909578Notes

Reaction equation

HRID 1909578 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([O:22][CH:23]([CH3:25])[CH3:24])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([O:22][CH:23]([CH3:24])[CH3:25])[CH:10]=1

Participants

5

Reactant 2

HCID 58566403(E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58566451Ethyl 3-(4-hydroxy-2 isopropoxyphenyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To (E)-ethyl 3-(4-(benzyloxy)-2-isopropoxyphenyl)acrylate (699) (530 mg, 1.56 mmol) in ethanol (12 mL) was added Pd/C (0.5 eq, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight at room temperature, filtered through a pad of celite and concentrated in vacuo to give ethyl 3-(4-hydroxy-2 isopropoxyphenyl)propanoate (700).

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ca0faa5e39940f0bd2a8442de6dc47d
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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