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

HRID 1883981Notes

Reaction equation

HRID 1883981 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 6.25 N 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, ethylCH2), 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-9d86dd5584e74755a65a52972f68d378
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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