Hydrochloric Acid → 3-Phenyl-5-butyrylisoxazole

HRID 345179

Reaktionsgleichung

Reaktionsgleichung von HRID 345179
[OH:1][CH:2]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)[CH2:3][CH2:4][CH3:5].Cl[O-].[Na+].N1C=CC=CC=1.Cl>ClCCl>[C:2]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)(=[O:1])[CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 108893475-(1-Hydroxybutyl)-3-phenylisoxazoleHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 101306023-Phenyl-5-butyrylisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

In 12.5 ml of dichloromethane, 4.4 g (20 mmol) of 5-(1-hydroxybutyl)-3-phenylisoxazole were dissolved. While the solution was being stirred, 35.2 g (60 mmol) of a 12.7% aqueous solution of sodium hypochlorite were added dropwise to the solution. Next, a liquid mixture which had been obtained by adding 0.48 g (6.1 mmol) of pyridine to 1.0 ml of 6N hydrochloric acid) was added dropwise over 1 hour and the reaction temperature was maintained at 20° C. After completion of the reaction, the organic layer was collected and was washed successively with a 5% aqueous solution of sodium hydrogensulfite, water and 1N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was then recrystallized from ethanol, whereby the target compound, namely, 5-butyryl-3-phenylisoxazole was obtained as crystals.

Aufarbeitung

  1. customNext, a liquid mixture which had been obtained
  2. additionwas added dropwise over 1 hour
  3. customAfter completion of the reaction
  4. customthe organic layer was collected
  5. washwas washed successively with a 5% aqueous solution of sodium hydrogensulfite, water and 1N hydrochloric acid
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was then recrystallized from ethanol, whereby the target compound

Quellen und Nachweise

ORD-Eintrag
ord-986bb4f03aa34f55917a406890616c22
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055585

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