2-[4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenoxy]-2-methyl-propionic Acid Ethyl Ester → 2-(2-Benzyl-4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 398170Notes

Reaction equation

HRID 398170 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][C:10]=1[CH:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:7])[CH3:6])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 693122172-[4-Benzyloxy-2-(hydroxy-phenyl-methyl)-phenoxy]-2-methyl-propionic Acid Ethyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 693104612-(2-Benzyl-4-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-[4-benzyloxy-2-(hydroxy-phenyl-methyl)-phenoxy]-2-methyl-propionic acid ethyl ester (1.67 g, 3.97 mmol maximum) in ethanol (50 mL) was treated with 5% Pd/C (0.42 g) and hydrogen (60 psi, room temperature, 18 h). The mixture was filtered and concentrated to a viscous colorless oil (1.15 g, 91%): 1H NMR (400 MHz, CDCl3) δ1.32 (t, 3H, J=7.1 Hz), 1.51 (s, 6H), 3.99 (s, 2H), 4.30 (q, 2H, J=7.0 Hz), 4.93 (brs, 1H), 6.58-6.66 (m, 3H), 7.22-7.34 (m, 5H); MS (ES) m/e 315 [M+1].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to a viscous colorless oil (1.15 g, 91%)

Sources & evidence

ORD record
ord-a9d5a840c08942959f79a8e497c7eea8
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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