Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]propanoate

HRID 1690608Notes

Reaction equation

HRID 1690608 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20]>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[O:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20]

Participants

3

Reactant 1

HCID 66907011Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate

Product 1

HCID 66907182Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]propanoateYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate (16 g, 57 mmol) was dissolved in ethanol (190 mL) in a Parr apparatus. Nitrogen was bubbled for 15 minutes and Pd/C 10% (0.8 g) was added. The reaction mixture was submitted to hydrogenation under H2 atmosphere (3 bars) until the end of H2 consumption. The palladium was then filtered and the solvent was evaporated under reduced pressure to yield 12.3 g (76%) of the desired product as a colorless oil.

Workup

  1. customNitrogen was bubbled for 15 minutes
  2. additionPd/C 10% (0.8 g) was added
  3. customuntil the end of H2 consumption
  4. filtrationThe palladium was then filtered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-daceb19e62f74f98af860b07cf6a5017
Source dataset
uspto-grants-2012_04
Patent number
US08153647B2

Reaction notes

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