4-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester → 4-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid

HRID 2225635Notes

Reaction equation

HRID 2225635 reaction equation
C[O:2][C:3](=[O:23])[C:4](=[O:22])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:7][CH:6]=1>CO.[OH-].[Na+]>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][CH2:12][O:11][C:8]2[CH:9]=[CH:10][C:5]([C:4](=[O:22])[C:3]([OH:23])=[O:2])=[CH:6][CH:7]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 541988504-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190044724-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acidYield 77.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[[3-(4-fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.58 g) in methanol and 0.5N sodium hydroxide (8 mL) was treated as in Example 19. Extraction provided 0.55 g which solidified and was crystallized from diethyl etherhexane to give 0.43 g of colorless 4-[[3-(4-fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid, mp 77°-78° C.

Workup

  1. additionwas treated as in Example 19
  2. extractionExtraction
  3. customprovided 0.55 g which
  4. customwas crystallized from diethyl etherhexane

Sources & evidence

ORD record
ord-204eb29e15b14e779b6304c9e3a0686d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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