Potassium Hydroxide → 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid

HRID 1684527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684527
[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10]CC)=[O:9].[OH-].[K+]>O.C(O)C>[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([OH:10])=[O:9]

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 12914722Ethyl 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate

Produkt 1

HCID 31593757-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

3.0 g (17.8 mmol) of ethyl 7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate are suspended in 10 ml of water and 20 ml of ethanol. The temperature is kept below 20° C. by cooling with ice, while 3.5 g (62.3 mmol) of potassium hydroxide are added. The mixture is stirred for 2 hours at ambient temperature, the ethanol is distilled off at a bath temperature of 30° C. and the aqueous solution is extracted with ethyl acetate. The aqueous phase is acidified to a pH of 6 while cooling with ice and shaken with dichloromethane, then the combined organic extracts are dried and evaporated down. 0.8 g (32% of theory) of the title compound are obtained as a brown oil.

Aufarbeitung

  1. customis kept below 20° C.
  2. additionare added
  3. distillationthe ethanol is distilled off at a bath temperature of 30° C.
  4. extractionthe aqueous solution is extracted with ethyl acetate
  5. temperaturewhile cooling with ice
  6. stirringshaken with dichloromethane
  7. customthe combined organic extracts are dried
  8. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-b635dd3125de4cb2995c963161e3dd0e
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641784

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