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

HRID 1719414Notes

Reaction equation

HRID 1719414 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][O: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][O: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 13504776[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester

Product 1

HCID 13504777[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acidYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2.3 g of [[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester and 43 ml of 1N sodium hydroxide in 86 ml of methanol was stirred at reflux for 1 hour. The methanol was removed and aqueous solution was acidified to pH 3. The precipitate was extracted with methylene chloride, washed with water, dried (magnesium sulfate) and concentrated in vacuo to give an oil. The oil was triturated with ether to yield 1.9 g, mp 121°-122° C. (84%) of [[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid.

Workup

  1. temperatureat reflux for 1 hour
  2. customThe methanol was removed
  3. extractionThe precipitate was extracted with methylene chloride
  4. washwashed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customThe oil was triturated with ether

Sources & evidence

ORD record
ord-e27d033ec27b49b3bd8f94d203fb24fe
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

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