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

HRID 1377035Notes

Reaction equation

HRID 1377035 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-3336a77faa4d4305a6aa989e17682140
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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