HCID 43423278, compound → (2-Propyl-phenoxy)-acetic Acid Ethyl Ester

HRID 898482Notes

Reaction equation

HRID 898482 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH:14]=[CH2:15])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH3:15])[CH3:2]

Participants

5

Reactant 2

HCID 43423278HCID 43423278, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20768112(2-Propyl-phenoxy)-acetic Acid Ethyl EsterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (2-allyl-phenoxy)-acetic acid ethyl ester (5.8 g, 26.3 mmol) in ethanol (200 mL) was treated with 5% Pd/C (59 mg) and hydrogen at ambient temperature for overnight. The mixture was filtered and concentrated to give the title compound (5.7 g, 98%). 1H NMR (400 MHz, CDCl3) • 7.16˜7.10 (m, 2H), 6.94˜6.89 (m, 1H), 6.71 (d, J=8.1 Hz, 1H), 4.53 (s, 2H), 4.26 (q, J=7.2 Hz, 2H), 2.65 (t, J=7.7 Hz, 2H), 1.71˜1.60 (m, 2H), 1.29 (t, J=7.0 Hz, 2H), 0.96 (t, J=7.0 Hz, 3H); MS (ES) m/e 406.18 (M++1).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ee7346d7f34e45eaace2a9de7b3ced70
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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