2-(5-Benzyloxy-2-but-1-enylphenoxy)-2-methylpropionic Acid Ethyl Ester → 2-(2-Butyl-5-hydroxyphenoxy)-2-methylpropionic acid ethyl ester

HRID 398186Notes

Reaction equation

HRID 398186 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[C:5]([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[CH:23]=[CH:24][CH2:25][CH3:26])([CH3:7])[CH3:6])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[C:5]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH2:23][CH2:24][CH2:25][CH3:26])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 693103232-(5-Benzyloxy-2-but-1-enylphenoxy)-2-methylpropionic Acid Ethyl EsterHCID 178418361HCID 178418361, compound

Product 1

HCID 693120282-(2-Butyl-5-hydroxyphenoxy)-2-methylpropionic acid ethyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(5-Benzyloxy-2-but-1-enylphenoxy)-2-methylpropionic acid ethyl ester (0.76 g, 2.06 mmol) in ethanol (50 mL) was treated with 5% Pd/C (0.10 g) and hydrogen (60 psi) at ambient temperature for 6 h. The mixture was filtered and concentrated in vacuo to give a colorless oil (0.52 g, 90%). 1H NMR (400 MHz, CDCl3) δ6.96 (d, J=7.8 Hz, 1H), 6.37 (dd, J=8.3, 2.4 Hz, 1H), 6.20 (s, 1H), 4.66 (br s, 1H), 4.24 (q, J=7.2 Hz, 2H), 2.53 (t, J=7.8 Hz, 2H), 1.60 (s, 6H), 1.53 (quintet, J=7.6 Hz, 2H), 1.34 (sextet, J=7.3 Hz, 2H), 1.25 (t, 7.1 Hz, 3H), 0.92 (t, J=7.3 Hz, 3H), MS (ES) m/e 281 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87748064deda4cb9854d7f09832c713d
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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