Ethyl Acetate → HCID 22505827, Verbindung

HRID 413457

Reaktionsgleichung

Reaktionsgleichung von HRID 413457
[CH3:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:11])=[O:10])=[CH:5][CH:4]=1.[CH3:12][C:13]1([CH3:22])[N:18]([O])[C:17]([CH3:21])([CH3:20])[CH2:16][CH2:15][CH2:14]1.C([O:25]C(=O)C)C>[Mo](=O)(=O)=O.O>[CH3:12][C:13]1([CH3:22])[CH2:14][CH2:15][CH2:16][C:17]([CH3:21])([CH3:20])[N:18]1[O:10][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([C:2](=[O:25])[CH3:1])=[CH:4][CH:5]=1)[CH3:11]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 136424'-EthylacetophenoneHCID 2724126Tempo

Produkt 1

HCID 22505827HCID 22505827, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14802Molybdenum trioxideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

,A mixture of 4-ethylacetophenone (23 g), 2,2,6,6-tetramethylpiperidine-1-oxyl (10,7 g) and molybdenum(VI)oxide (0,67 g) are purged with Argon for one hour. The mixture is then heated up to 70° C. and the solution prepared under A) is added drop wise under stirring within 5 minutes. Pressure is reduced to 300 mbar and the mixture is heated for 18 hours at 70° C. After the+reaction is completed the mixture is cooled to room temperature and the pressure is allowed to raise to normal pressure. Ethylacetate and water is added. The water phase is separated and extracted three times with ethylacetate. The organic phases are combined, washed with water, dried over Magnesium sulfate and concentrated. Excessive amounts of 2-(4-ethyl-phenoxymethyl)-oxirane are removed at 40° C./0,2 mbar. The raw product is subsequently chromatographically purified on silica with petrolether/ethylacetate=95/5 as eluent. A white+powder is obtained after recrystalization from pentane, corresponding to the compound of formula (104), having a melting point of 61.5-63° C.

Aufarbeitung

  1. customare purged with Argon for one hour
  2. customthe solution prepared under A)
  3. additionis added drop wise
  4. temperaturethe mixture is heated for 18 hours at 70° C
  5. customAfter the+reaction
  6. temperatureis cooled to room temperature
  7. temperatureto raise to normal pressure
  8. customThe water phase is separated
  9. extractionextracted three times with ethylacetate
  10. washwashed with water
  11. dry with materialdried over Magnesium sulfate
  12. concentrationconcentrated
  13. customExcessive amounts of 2-(4-ethyl-phenoxymethyl)-oxirane are removed at 40° C./0,2 mbar
  14. customThe raw product is subsequently chromatographically purified on silica with petrolether/ethylacetate=95/5 as eluent
  15. customA white+powder is obtained
  16. customafter recrystalization from pentane

Quellen und Nachweise

ORD-Eintrag
ord-447b3434eb0044ef84aa622873a81f7e
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566468B1

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