Ethyl Acetate → Ethyl 2-(4-hydroxyphenoxy)acetate

HRID 1824315Notes

Reaction equation

HRID 1824315 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[CH3:2].CCOC(C)=O>[Pd].CCO>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 734886Ethyl [4-(Benzyloxy)phenoxy]acetate

Product 1

HCID 13187337Ethyl 2-(4-hydroxyphenoxy)acetateYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl-4-benzyloxyphenoxyacetate compound (3.50 g, 12.2 mmol) was placed in a PARR bottle along with EtOAc (75 mL), EtOH (75 mL), and 5% Pd/C (1.20 g) and the mixture placed under 40 psi of H2. The reaction was shaken under pressure for 4 hours after which no starting material remained by TLC. The catalyst was removed by filtration through Celite and the filtrate concentrated in vacuo to give 2.35 g (97%) of the desired phenol. MP

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-62689a56859a41dda62a6d0199b13252
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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