Hydrochloric Acid → 4-[[2-(3,4-Dimethoxyphenoxy)ethyl]oxy]-alphaoxobenzeneacetic acid

HRID 2225666Notes

Reaction equation

HRID 2225666 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[CH:7][CH:6]=1.Cl>CO.[OH-].[Na+]>[CH3:24][O:23][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[O:21][CH3:22])[O:14][CH2:13][CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:25])[C:3]([OH:26])=[O:2])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 545023044-[[2-(3,4-Dimethoxyphenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190043994-[[2-(3,4-Dimethoxyphenoxy)ethyl]oxy]-alphaoxobenzeneacetic acidYield 93.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[[2-(3,4-dimethoxyphenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.7 g) in methanol and 0.5N sodium hydroxide (8 mL) was heated on the steam bath for 0.5 hours and cooled. 2N hydrochloric acid (5 mL) was added and the resulting solids were filtered and washed with water. The solids were dried by boiling in benzene (20 mL), filtered, hexane (5 mL) was added, and the resulting mixture was chilled to give 0.63 g of colorless 4-[[2-(3,4-dimethoxyphenoxy)ethyl]oxy]-alphaoxobenzeneacetic acid, mp 140°-141° C.

Workup

  1. temperaturewas heated on the steam bath for 0.5 hours
  2. temperaturecooled
  3. filtrationthe resulting solids were filtered
  4. washwashed with water
  5. customThe solids were dried
  6. filtrationfiltered
  7. additionhexane (5 mL) was added
  8. temperaturethe resulting mixture was chilled

Sources & evidence

ORD record
ord-6116a9c094494479b239b215cfb55ad3
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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