Hydrochloric Acid → [(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid

HRID 370988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 370988
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]([C:14](=[O:16])[CH3:15])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl.C(OCC)C>C(O)C>[C:14]([C:12]1[S:11][C:10]2[C:17]([Cl:20])=[C:18]([Cl:19])[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[CH:8][C:9]=2[CH:13]=1)(=[O:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53636860Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate

Produkt 1

HCID 13290041[(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acidAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 5.1 g of ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate in 200 ml of 95% ethanol is added 150 ml of a 6N sodium hydroxide solution and the mixture is refluxed at 100° for 45 mins. The solvent is removed in vacuo to give a white slurry to which is added 250 ml of a 6N hydrochloric acid and 200 ml ethyl ether. The mixture is stirred for 2 hrs, filtered and the filter cake is distributed between 6N hydrochloric acid and ethyl ether. The organic layers are separated and the aqueous layers are extracted with ethyl ether. The combined organic extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is evaporated to give a solid. Recrystallization from acetone-hexane gives 2.2 g of [(2-acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid, mp 203°-205°.

Aufarbeitung

  1. temperaturethe mixture is refluxed at 100° for 45 mins
  2. customThe solvent is removed in vacuo
  3. customto give a white slurry to which
  4. filtrationfiltered
  5. customThe organic layers are separated
  6. extractionthe aqueous layers are extracted with ethyl ether
  7. washThe combined organic extracts are washed
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent is evaporated
  11. customto give a solid
  12. customRecrystallization from acetone-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4486fcdfcdcc4f4aa1030d1c5c230e87
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04528399

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