Potassium Hydroxide → 4-Methyl-1-oxo-1H-2-benzopyran-3-carboxylic acid

HRID 259253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259253
[C:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])(=O)[CH3:2].Br[CH:14](C(OCC)=O)[C:15]([O:17]CC)=[O:16].[OH-].[K+]>C(O)C>[CH3:2][C:1]1[C:4]2[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[O:8][C:14]=1[C:15]([OH:17])=[O:16]

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 684742-Acetylbenzoic acidHCID 69637Diethyl bromomalonate

Produkt 1

HCID 123882954-Methyl-1-oxo-1H-2-benzopyran-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 2- acetylbenzoic acid (6.21g), diethyl bromomalonate (9.0g.) and potassium hydroxide (2.12g.) in ethanol (50ml.) was heated under reflux for 6 hours. The cooled mixture was evaporated to dryness, water (100ml.) added and extracted with ether. The combined ethereal extracts were washed with water, dried and evaporated to dryness. The residue was heated under reflux with a mixture of concentrated hydrochloric acid (160ml.) -- acetic acid (100ml.) for two hours, cooled poured into iced water (1 liter). Filtration gave the product as a white solid, mp. 250° -2°, (lit mp. 248° -9°) (Found: C, 64.59; H, 4.01. C11H8O4 requires C, 64.70; H, 3.95).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe cooled mixture was evaporated to dryness, water (100ml.)
  4. additionadded
  5. extractionextracted with ether
  6. washThe combined ethereal extracts were washed with water
  7. customdried
  8. customevaporated to dryness
  9. temperatureThe residue was heated
  10. temperatureunder reflux with a mixture of concentrated hydrochloric acid (160ml.)
  11. temperaturecooled
  12. additionpoured into iced water (1 liter)
  13. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-1a9e4bed730a48dfb4c25b62fccca76d
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04036964

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