Sodium Hydroxide → [[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-2-naphthalenyl]oxy]acetic acid

HRID 465146Notes

Reaction equation

HRID 465146 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:36](=[O:38])[CH3:37])[C:10]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[Na+]>CO>[C:36]([C:9]1[C:10]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=2[CH2:33][CH2:34][CH3:35])=[CH:11][CH:12]=[C:13]2[C:8]=1[CH:7]=[C:6]([O:5][CH2:4][C:3]([OH:39])=[O:2])[CH:15]=[CH:14]2)(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13505605[[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)-pentyloxy]-2-naphthalenyl]oxy]acetic acid methyl ester

Product 1

HCID 13505606[[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-2-naphthalenyl]oxy]acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.45 g of [[8-acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-2-naphthalenyl]oxy]acetic acid methyl ester in 54 ml of methanol, was added 27 ml of 1N sodium hydroxide. The reaction mixture was stirred at reflux for one hour and 20 minutes. The methanol was removed in vacuo and the aqueous residue was acidified to pH3. The precipitate was dissolved in chloroform, dried (magnesium sulfate), and the solid obtained from the concentrated chloroform solution was recrystallized from ethylacetate-hexane to yield 1.1 g, mp 103°-106° C. (78%) of [[8-Acetyl-7-[5-(4-acetyl-3-hydroxy-2-propylphenoxy)pentyloxy]-2-naphthalenyl]oxy]acetic acid.

Workup

  1. temperatureat reflux for one hour and 20 minutes
  2. customThe methanol was removed in vacuo
  3. dissolutionThe precipitate was dissolved in chloroform
  4. dry with materialdried (magnesium sulfate)
  5. customthe solid obtained from the concentrated chloroform solution
  6. customwas recrystallized from ethylacetate-hexane

Sources & evidence

ORD record
ord-68a31c31bc8d44fcbc3437dc8eac7873
Source dataset
uspto-grants-1985_10
Patent number
US04550190

Reaction notes

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