HCID 86760506, compound → HCID 17861374, compound

HRID 1294131Notes

Reaction equation

HRID 1294131 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][C:10]=1/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])C1C=CC=CC=1>[C].[Pd].O1CCCC1>[CH2:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:11]=1)[CH3:17]

Participants

4

Reactant 1

HCID 86760506HCID 86760506, compound

Product 1

HCID 17861374HCID 17861374, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (E)-3-(2-benzyloxy-5-ethoxyphenyl)-2-propenoate (4.58 g), 5% palladium carbon (6.0, g) and tetrahydrofuran (100 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give ethyl 3-(5-ethoxy-2-hydroxyphenyl)propionate as a colorless oil (3.15 g, 94%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter filtering off the catalyst
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bd934548a11c4a30bd38532671d35e51
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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