Sodium Hydroxide → 4-[[4-(2Naphthalenyloxy) butyl]oxy]-alpha-oxobenzeneacetic acid

HRID 2225689Notes

Reaction equation

HRID 2225689 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][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.CC(C)=O>[CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:25]=[CH:26][C:17]=1[O:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4](=[O:27])[C:3]([OH:28])=[O:2])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 537942984-[[4-(2-Naphthalenyloxy)butyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190043814-[[4-(2Naphthalenyloxy) butyl]oxy]-alpha-oxobenzeneacetic acidYield 49.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A mixture of 4-[[4-(2-naphthalenyloxy)butyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.9 g) in methanol (15 mL), acetone (5 mL), and 0.5N sodium hydroxide (10 mL) was treated as in Example 19. Extraction with dichloromethane provided material which was crystallized from diethyl ether-hexane to give 0.43 g of colorless 4-[[4-(2naphthalenyloxy) butyl]oxy]-alpha-oxobenzeneacetic acid, mp 133°-135°C.

Workup

  1. additionwas treated as in Example 19
  2. extractionExtraction with dichloromethane provided material which
  3. customwas crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-9a81f7aec5924c83841231684e68156f
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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