Sodium Hydroxide → [(6,7-Dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid

HRID 1903512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1903512
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:18]([Cl:19])=[C:17]([Cl:20])[C:10]2[S:11][C:12]([CH:14]([OH:16])[CH3:15])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+]>C(O)C>[Cl:19][C:18]1[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]([OH:16])[CH3:15])[S:11][C:10]=2[C:17]=1[Cl:20]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 13290073Ethyl [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate

Produkt 1

HCID 13290074[(6,7-Dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acidAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 16 g of ethyl[ (6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetate in 300 ml 95% ethanol is added 300 ml of a 6 N sodium hydroxide and the mixture is refluxed at 100° for 30 mins. The cooled mixture is concentrated to a white slurry which is diluted with 200 ml of ice-water and 200 ml of ethyl ether. With stirring and efficient cooling, the mixture is acidified with 6 N hydrochloric acid. The acidic mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the crude product from acetone and hexane gives 11.4 g of [(6,7-dichloro-2-(1-hydroxyethyl)benzo[b]thien-5-yl)oxy]acetic acid, mp 173°-175°.

Aufarbeitung

  1. temperaturethe mixture is refluxed at 100° for 30 mins
  2. concentrationThe cooled mixture is concentrated to a white slurry which
  3. additionis diluted with 200 ml of ice-water and 200 ml of ethyl ether
  4. extractionThe acidic mixture is extracted with ethyl ether
  5. washThe ether extracts are washed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customRecrystallization of the crude product from acetone and hexane

Quellen und Nachweise

ORD-Eintrag
ord-5d99eb0aa40d4119bde45a1892b85549
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436748

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