(E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester → Ethyl 3-(4-hydroxy-2-methylphenyl)propanoate

HRID 1391777Notes

Reaction equation

HRID 1391777 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]CC2C=CC=CC=2)[CH:5]=[CH:4][C:3]=1/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Pd].CCO>[OH:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 1

HCID 21986386(E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester

Product 1

HCID 21986481Ethyl 3-(4-hydroxy-2-methylphenyl)propanoateYield 63.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask containing 10% Pd/C catalyst under nitrogen was added ethyl (2E)-3-{2-methyl-4-[(phenylmethyl)oxy]phenyl}-2-propenoate (1.22 g, 4.12 mmol) in EtOH (15 mL) washing in with more EtOH (2×4 mL). The reaction vessel was placed under an atmosphere of hydrogen and stirred rapidly at ambient temperature for 19 h. The mixture was then filtered through a pad of celite washing with EtOH and the filtrate reduced under vacuum. The residue was the purified by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 10:1 to 2:1) to afford the title compound (548 mg).

Workup

  1. washwashing in with more EtOH (2×4 mL)
  2. filtrationThe mixture was then filtered through a pad of celite
  3. washwashing with EtOH
  4. custompurified by SPE (silica, 20 g cartridge)
  5. washeluting with cyclohexane

Sources & evidence

ORD record
ord-1266848e6ec14661bb0453ddcccfd503
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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