HCID 69313172, compound → (2-Ethyl-4-hydroxyphenoxy)acetic Acid Ethyl Ester

HRID 1609961Notes

Reaction equation

HRID 1609961 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC2C=CC=CC=2)=[CH:9][C:8]=1[CH:21]=[CH2:22])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH2:21][CH3:22])[CH3:2]

Participants

5

Reactant 2

HCID 69313172HCID 69313172, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58580457(2-Ethyl-4-hydroxyphenoxy)acetic Acid Ethyl EsterYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (4-benzyloxy-2-vinylphenoxy)acetic acid ethyl ester (0.55 g, 1.77 mmol) in ethanol (15 mL) was treated with 5% Pd/C (70 mg) and hydrogen (60 psi) at ambient temperature for 18 h. The mixture was filtered and concentrated in vacuo to give a tan oil (0.31 g, 77%): 1H NMR (400 MHz, CDCl3) δ 6.68 (d, J=2.9 Hz, 1H), 6.62 (d, J=8.8 Hz, 1H), 6.57 (dd, J=8.8, 2.9 Hz, 1H), 4.62 (s, 1H), 4.57 (s, 2H), 4.25 (q, J=7.2 Hz, 2H), 3.73 (q, J=7.0 Hz, 2H), 2.66 (q, J=7.7 Hz, 2H), 1.34-0.92 (m, 6H); MS (FIA) m/e 225 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20f93b696bb345c8aa294e305f200e73
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

Loading…