4-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester → 4-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid

HRID 2225695Notes

Reaction equation

HRID 2225695 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][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1>CO.[OH-].[Na+]>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[CH2:14][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

4

Reactant 1

HCID 540032964-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190044194-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acidYield 86.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-[[3-(2-naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.6 g) in methanol (10 mL) and 0.5N sodium hydroxide (4 mL) was treated as in Example 19. Extraction with dichloromethane provided material which was crystallized from dichloromethane-hexane to give 0.5 g of colorless 4-[[3-(2-naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid, mp 123°-124° C.

Workup

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

Sources & evidence

ORD record
ord-1a0c2605c9254d61910b78dc97deaf35
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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