Sulfuric Acid → 10-Cycloeicosenone

HRID 1883286

Reaktionsgleichung

Reaktionsgleichung von HRID 1883286
[OH:1][CH:2]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C1(C)C=CC=CC=1.S(=O)(=O)(O)O>[Zn].O>[C:2]1(=[O:1])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 673128522-Hydroxy-11-cycloeicosenone

Produkt 1

HCID 6731346910-CycloeicosenoneAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a 50 ml four neck reactor equipped with a thermometer, a dripping funnel and a refrigerant, zinc powder (2.3 g), 2-hydroxy-11-cycloeicosenone (1.4 g) and toluene (10 ml) were mixed, stirred and heated at 90° C. under nitrogen flow. A 20N sulphuric acid aqueous-solution (2.8 ml) was added thereto dropwise over 2.5 hours and the resulting mixture was stirred under heating for 30 minutes. Toluene and water were added after the reaction and the resulting solution was allowed to stand to separate into two phases. The organic phase was washed twice with water and then washed with a saturated sodium chloride aqueous solution. The solvent was removed under reduced pressure to give 1.4 g of crude product. The crude product was purified on a silica gel column chromatograph (hexane/ethyl acetate=10/1, v/v) to give 1.2 g of 10-cycloeicosenone (yield 92%).

Aufarbeitung

  1. stirringthe resulting mixture was stirred
  2. temperatureunder heating for 30 minutes
  3. customafter the reaction
  4. customto separate into two phases
  5. washThe organic phase was washed twice with water
  6. washwashed with a saturated sodium chloride aqueous solution
  7. customThe solvent was removed under reduced pressure
  8. customto give 1.4 g of crude product
  9. customThe crude product was purified on a silica gel column chromatograph (hexane/ethyl acetate=10/1

Quellen und Nachweise

ORD-Eintrag
ord-13f9e2294eca4c6db11810efce91b7e2
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759557B2

Verknüpfte Notizen

Wird geladen…