Cyclopropanecarboxylic acid → n-Butyl cyclopropyl ketone

HRID 66407

Reaktionsgleichung

Reaktionsgleichung von HRID 66407
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10]>CCOCC>[CH:1]1([C:4]([CH2:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 15655Cyclopropanecarboxylic acidHCID 178418339Butyllithium

Produkt 1

HCID 11029852n-Butyl cyclopropyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a vigorously-stirred solution of 31.0 g of cyclopropanecarboxylic acid in 330 ml of ether is added a solution of n-butyllithium (748 mmoles) in ca. 750 ml. of 2:1 ether-hexane during 1 hour at 5-10° C. The resulting suspension is diluted with 300 ml of ether and stirred at room temperature for 2 hours and at reflux for 2 hours. The mixture is cooled and poured into several portions of 1:1 ice - 4N hydrochloric acid. The ethereal phases are combined and washed with brine, sodium carbonate solution, and brine. The extract is dried over magnesium sulfate and concentrated. The residue is distilled to provide a liquid, b.p. 102°-104° C. (80 mm), pmr spectrum (CDCl3):δ2.55 (triplet, --CH2CO--).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture is cooled
  3. washwashed with brine, sodium carbonate solution, and brine
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue is distilled
  7. customto provide a liquid, b.p. 102°-104° C. (80 mm), pmr spectrum (CDCl3)

Quellen und Nachweise

ORD-Eintrag
ord-8b0fdf1f53984ba8a92265806892d021
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04131737

Verknüpfte Notizen

Wird geladen…