3-(4-Benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester → 3-(4-Hydroxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester

HRID 2212559Notes

Reaction equation

HRID 2212559 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:23])([CH3:22])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14]CC2C=CC=CC=2)=[CH:10][CH:9]=1)=[O:7])[CH3:2]>CO>[CH2:1]([O:3][C:4](=[O:24])[C:5]([CH3:23])([CH3:22])[C:6]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1)=[O:7])[CH3:2]

Participants

3

Reactant 1

HCID 695965083-(4-Benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester

Product 1

HCID 695963983-(4-Hydroxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 3-(4-benzyloxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester (1.0 g, 3.07 mmol) was taken up in methanol (10 mL) and ethyl acetate (10 mL), nitrogen gas was bubbled though the solution for 15 min, and 10% Pd/C catalyst was added. The reaction was charged with hydrogen to 40 PSI and shaken for 5 h. The reaction was filtered though Celite® and concentrated to give 3-(4-hydroxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester (0.724 g, 100%) as an oil. MS found: (M+H)+=237.

Workup

  1. customethyl acetate (10 mL), nitrogen gas was bubbled though the solution for 15 min
  2. addition10% Pd/C catalyst was added
  3. additionThe reaction was charged with hydrogen to 40 PSI
  4. filtrationThe reaction was filtered though Celite®
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3dcf7b7dafa745159530e0e68f2f2554
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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