Methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetate → Methyl 2-(5-ethoxy-2-hydroxyphenyl)acetate

HRID 1294130Notes

Reaction equation

HRID 1294130 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[CH2:18][C:19]([O:21][CH3:22])=[O:20])C1C=CC=CC=1>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH3:17])=[CH:11][C:10]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

4

Reactant 1

HCID 17861303Methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetate

Product 1

HCID 17861247Methyl 2-(5-ethoxy-2-hydroxyphenyl)acetateYield 73.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetate (1.60 g), 5% palladium carbon (3.0 g) and tetrahydrofuran (50 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure. Hexane was added to the obtained crystals and the mixture was filtrated to give crystals (0.82 g) of methyl 2-(2-hydroxy-5-ethoxyphenyl)acetate. Recrystallization from diisopropyl ether-hexane gave pale-yellow prism crystals. melting point: 83-84° C.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter filtering off the catalyst
  3. customthe solvent was evaporated under reduced pressure
  4. additionHexane was added to the obtained crystals
  5. filtrationthe mixture was filtrated

Sources & evidence

ORD record
ord-494d51de0a744ba9b3ea26724663883b
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…