3-(4-Benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester → 3-Hydroxy-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester

HRID 2212565Notes

Reaction equation

HRID 2212565 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH:4]([CH3:21])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][CH:8]=1)[OH:6].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:22])[CH:4]([CH3:21])[CH:5]([OH:6])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 695964413-(4-Benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 623934773-Hydroxy-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl esterYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C was added to a degassed solution of 3-(4-benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester (0.335 g, 1.1 mmol) in methanol (30 mL) and charged to 50 PSI hydrogen, then shaken for 2.5 h. The reaction was filtered to remove the catalyst and concentrated to give 3-hydroxy-3-(4-hydroxy-phenyl)-2-methyl-propionic acid methyl ester (0.242 g, 100%) as an oil. MS found: (M+H)+=211.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the catalyst
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-91687b1e531340e6bd403277c77ffb25
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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