Ethyl [4-(Benzyloxy)phenoxy]acetate → Ethyl 2-(4-hydroxyphenoxy)acetate

HRID 412611Notes

Reaction equation

HRID 412611 reaction equation
C([O:8][C:9]1[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>O1CCCC1.[C].[Pd]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 734886Ethyl [4-(Benzyloxy)phenoxy]acetate

Product 1

HCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateYield 93%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethy 4-benzyloxyphenoxyacetate (21.78 g) was hydrogenated using 7.5% palladium carbon (3.2 g) in tetrahydrofuran (220 ml) at 3 atm over 7 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. The obtained solid was filtrated with diisopropyl ether and dried under reduced pressure to give the title compound (13.88 g) as a white solid.

Workup

  1. customover 7 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. customthe solvent was evaporated
  5. filtrationThe obtained solid was filtrated with diisopropyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-390a83ce644c42a3870cb720e20bb370
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…