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

HRID 1242389Notes

Reaction equation

HRID 1242389 reaction equation
[CH2:1]([O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[CH3:21])[CH3:2]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:21])[CH3:2]

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 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5 g (16.8 mmol) of the above prepared (E)-3-(4-benzyloxy-2-methyl-phenyl)-acrylic acid ethyl ester was dissolved in 50 ml of tetrahydrofuran and hydrogenated over 0.8 g of 10% of palladium on charcoal as catalyst at ambient temperature and atmospheric pressure. Filtering off the catalyst and evaporating the solvent yielded 3.5 g of the title compound as light yellow oil (100% of theory).

Workup

  1. filtrationFiltering off the catalyst
  2. customevaporating the solvent

Sources & evidence

ORD record
ord-cec737d87c654c609e59bcc912643ce3
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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