Sodium Hydroxide → (E)-4-[[3-(2-naphthalenyl)-2-propenyl]oxy]-alpha-oxobenzeneacetic acid

HRID 2225697Notes

Reaction equation

HRID 2225697 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]/[CH:13]=[CH: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.[OH-].[Na+]>CO.CC(C)=O>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1/[CH:14]=[CH: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 14798Sodium HydroxideHCID 67757685HCID 67757685, compound

Product 1

HCID 19004263(E)-4-[[3-(2-naphthalenyl)-2-propenyl]oxy]-alpha-oxobenzeneacetic acidYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A mixture of (E)-4-[[3-(2-naphthalenyl)-2-propenyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.85 g) in methanol (20 mL), acetone (5 mL), and 0.5N sodium hydroxide (6 mL) was treated as in Example 19. Extraction with dichloromethane provided material which was crystallized from dichloromethane-hexane to give 0.75 g of colorless (E)-4-[[3-(2-naphthalenyl)-2-propenyl]oxy]-alpha-oxobenzeneacetic acid, mp 142°-143° 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-708f79de55a14882bd13c9eb3c251fc7
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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