HCID 53945181, Verbindung → [6-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid

HRID 2164922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2164922
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][CH:9]=[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])[C:7]=1[CH2:33][CH2:34][CH3:35]>CO.[OH-].[Na+]>[C:12]([C:11]1[C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH2:33][CH2:34][CH3:35])[C:8]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([C:26](=[O:28])[CH3:27])=[C:22]([OH:29])[C:21]=2[CH2:30][CH2:31][CH3:32])=[CH:9][CH:10]=1)(=[O:14])[CH3:13]

Komponenten

4

Edukt 1

HCID 53945181HCID 53945181, Verbindung

Produkt 1

HCID 13389155[6-Acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 1.41 g of [6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid methyl ester in 50 ml of methanol and 14 ml of 1N sodium hydroxide was stirred at reflux for 22 hours. The methanol was removed in vacuo and the pH of the residue was adjusted to 2.0 with 6N hydrochloric acid. The gummy product was extracted with ether and the crude extract was purified by chromatography on 60 g of silica gel. Elution with a solvent mixture of toluene:ethyl acetate:acetic acid (65:25:10) gave, after recrystallization from methylene chlorideether, 0.51 g (38%), mp 151°-155°, of [6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-propylphenoxy]acetic acid.

Aufarbeitung

  1. temperatureat reflux for 22 hours
  2. customThe methanol was removed in vacuo
  3. extractionThe gummy product was extracted with ether
  4. extractionthe crude extract
  5. customwas purified by chromatography on 60 g of silica gel
  6. washElution
  7. additionwith a solvent mixture of toluene:ethyl acetate:acetic acid (65:25:10)
  8. customgave
  9. customafter recrystallization from methylene chlorideether, 0.51 g (38%), mp 151°-155°

Quellen und Nachweise

ORD-Eintrag
ord-1f03882bb4f44ea29f3f5050d2f6af59
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04507498

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