4-[[2-[4-(1,1'-Biphenyl)oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester → alpha-Oxo-4-[[2-(4-phenoxyphenoxy)ethyl]oxy]benzeneacetic acid

HRID 2225663Notes

Reaction equation

HRID 2225663 reaction equation
C[O:2][C:3](=[O:28])[C:4](=[O:27])[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](C3C=CC=CC=3)=[CH:17][CH:16]=2)=[CH:7][CH:6]=1>CO.[OH-].[Na+]>[O:27]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([O:11][C:8]3[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=3)=[CH:19][CH:20]=2)=[CH:9][CH:10]=1)[C:3]([OH:2])=[O:28]

Participants

4

Reactant 1

HCID 538813354-[[2-[4-(1,1'-Biphenyl)oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 19004268alpha-Oxo-4-[[2-(4-phenoxyphenoxy)ethyl]oxy]benzeneacetic acidYield 136.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[[2-[4-(1,1'-biphenyl)oxy]ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.8 g) in methanol (20 mL) and 0.5N sodium hydroxide (8 mL) was treated as in Example 19. Extraction provided solids which were crystallized from diethyl etherhexane to give 0.55 g of colorless alpha-oxo-4-[[2-(4-phenoxyphenoxy)ethyl]oxy]benzeneacetic acid, mp 124°-126° C.

Workup

  1. additionwas treated as in Example 19
  2. extractionExtraction
  3. customprovided solids which
  4. customwere crystallized from diethyl etherhexane

Sources & evidence

ORD record
ord-e8f96ee4fb324cb29366838199d8a999
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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