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

HRID 1981990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981990
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]

Komponenten

4

Edukt 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

Produkt 1

HCID 13504777[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acidAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d0a33f8b81764659b6fcb56c08c5af16
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04594442

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