Hydrochloric Acid → 3-Hydroxy-5-(benzo[b]thien-5-yl)cyclohex-2-en-1-one

HRID 978317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978317
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[S:13]1[CH:17]=[CH:16][C:15]2[CH:18]=[C:19]([CH:22]=[CH:23][C:24](=[O:26])[CH3:25])[CH:20]=[CH:21][C:14]1=2.[OH-].[K+].Cl>C(O)C>[OH:4][C:3]1[CH2:2][CH:22]([C:19]2[CH:20]=[CH:21][C:14]3[S:13][CH:17]=[CH:16][C:15]=3[CH:18]=2)[CH2:23][C:24](=[O:26])[CH:25]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 573189081-(Benzo[b]thien-5-yl)but-1-en-3-one

Produkt 1

HCID 139858103-Hydroxy-5-(benzo[b]thien-5-yl)cyclohex-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Diethyl malonate (7.16 g) was added to a solution of sodium metal (1 equiv) in anhydrous absolute ethanol (40 ml). 1-(Benzo[b]thien-5-yl)but-1-en-3-one (8.7 g) was added to the solution and the mixture was heated under reflux for 2 hr. An aqueous solution of potassium hydroxide (5.3 g in 50 ml water) was added and the mixture was heated under reflux for a further 5 hr. The hot mixture was acidified by dropwise addition of a dilute aqueous hydrochloric acid solution. After cooling, the product was filtered off and dried by azeotropic distillation with toluene to give 3-hydroxy-5-(benzo[b]thien-5-yl)cyclohex-2-en-1-one as a yellow solid, mp 192° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 5 hr
  5. temperatureAfter cooling
  6. filtrationthe product was filtered off
  7. dry with materialdried by azeotropic distillation with toluene

Quellen und Nachweise

ORD-Eintrag
ord-7698de47685f46208cfa80a93c997e08
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04664693

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