HCID 15506059, compound → 2-(3-ethoxyphenyl)acetic acid

HRID 2258640Notes

Reaction equation

HRID 2258640 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([O:13]C)=[O:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2]>CO.[OH-].[Na+]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 15506059HCID 15506059, compound

Product 1

HCID 43159872-(3-ethoxyphenyl)acetic acidYield 103.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 3-ethoxyphenylacetate (92.6 g, 0.4 mole) in methanol (600 ml) and 6.25N NaOH (400 ml) was stirred overnight at room temperature and then filtered and concentrated in vacuo to remove the methanol. The solution was adjusted to pH 1 with concentrated HCl, the resulting precipitate filtered, washed with ice water, and dried under high vacuum to give 3-ethoxyphenyl acetic acid (74.5 g). M.p=89°-90° C. 1H NMR (DMSO-d6, 200 MHz) δ: 1.30 (6, J=7 Hz, 3H, CH3), 3.50 (s, 2H, ArCH2), 3.98 (q, J=7 Hz, 2H, ethyl CH2), 6.75-6.80 (m, 3H, Ar), 7.14-7.23 (m, 1H, Ar). (Lit. ref.: J. Med. Chem, 1980, 23(4) 437-444.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto remove the methanol
  4. filtrationthe resulting precipitate filtered
  5. washwashed with ice water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-e903579417e14701b510c8bad59adb49
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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