Hydrochloric Acid → [[6,7-Dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acid

HRID 370992Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370992
C([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[C:19]([Cl:20])=[C:18]([Cl:21])[C:10]2[S:11][C:12]([CH:14]([OH:17])[CH2:15][CH3:16])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl>C(O)C.C(OCC)C>[Cl:20][C:19]1[C:7]([O:6][CH2:5][C:4]([OH:22])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH:14]([OH:17])[CH2:15][CH3:16])[S:11][C:10]=2[C:18]=1[Cl:21]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13290046Ethyl [(6,7-dichloro-2-(1-hydroxypropyl]benzo[b]thien-5-yl]oxy]acetate

Produkt 1

HCID 13290047[[6,7-Dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acidAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 9.5 g of ethyl[[6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetate in 210 ml of ethanol is added 180 ml of 6N sodium hydroxide solution and the mixture is stirred at 100° for 30 mins. The cooled mixture is concentrated in vacuo to give a white slurry which is diluted with 400 ml of ice water and 300 ml of ethyl ether. With stirring and efficient cooling, the mixture is acidified with 6N hydrochloric acid. The acidic mixture is extracted with ethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate and evaporated to dryness. Recrystallization of the residue from ethyl ether and hexane gives 7.5 g of [[6,7-dichloro-2-(1-hydroxypropyl)benzo[b]thien-5-yl]oxy]acetic acid, mp 156°-158°.

Aufarbeitung

  1. concentrationThe cooled mixture is concentrated in vacuo
  2. customto give a white slurry which
  3. stirringWith stirring
  4. extractionThe acidic mixture is extracted with ethyl ether
  5. washThe ether extracts are washed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness
  8. customRecrystallization of the residue from ethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-879f1e8416e648fdb8c9ee2bff7e7d1d
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528399

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