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Sulfuric Acid → 3-(4-Methylphenyl)-5-butyrylisoxazole

HRID 1450652
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1450652
[H-].[Na+].C(C(C(OC1C=CC=CO1)=O)C(OC1C=CC=CO1)=O)C.[CH2:24]([CH:26]([C:30]([OH:32])=O)C(O)=O)[CH3:25].O1C=CCCC1.S(=O)(=O)(O)O.C(C(C([O-])=O)C([O-])=O)C.C(OC1C=CC=CO1)(=O)CC(OC1C=CC=CO1)=O.[Na].[CH3:73][C:74]1[CH:79]=[CH:78][C:77]([C:80]2[CH:84]=[C:83](C(Cl)=O)[O:82][N:81]=2)=[CH:76][CH:75]=1>C1C=CC=CC=1.O.C(O)(=O)C.O1CCCC1>[CH3:73][C:74]1[CH:75]=[CH:76][C:77]([C:80]2[CH:84]=[C:83]([C:30](=[O:32])[CH2:26][CH2:24][CH3:25])[O:82][N:81]=2)=[CH:78][CH:79]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

13

Edukt 8

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 11756Ethylmalonic acidHCID 24758Sodium hydrideHCID 6950106EthylpropanedioateHCID 19976934Dipyranyl ethylmalonateHCID 53715915
3-(4-Methylphenyl)isoxazole-5-carboxylic acid chloride
HCID 67715643Sodium dipyranyl malonate

Produkt 1

HCID 199769533-(4-Methylphenyl)-5-butyrylisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 50 ml of benzene, 2.6 g (57.5 mmol) of 60% sodium hydride were added to dipyranyl ethylmalonate which had been prepared from 5.7 g (43.2 mmol) of ethylmalonic acid, 9.0 g (107.1 mmol) of 3,4-dihydropyran and 1 droplet of concentrated sulfuric acid. At 40°-50° C., the ethylmalonate was converted to sodium dipyranyl malonate, to which a tetrahydrofuran solution of 3-(4-methylphenyl)isoxazole-5-carboxylic acid chloride synthesized above in the procedure (3) was added dropwise at room temperature. They were reacted for 3 hours. The reaction mixture was added with 10 ml of acetic acid and then heated under reflux for 6 hours. The mixture thus obtained was added into water and then extracted with benzene. The benzene extract was washed successively with an aqueous solution of sodium hydrogencarbonate and water. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off. Hexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole precipitated as crystals was collected by filtration.

Aufarbeitung

  1. customAt 40°-50° C.
  2. customsynthesized above in the procedure (3)
  3. additionwas added dropwise at room temperature
  4. customThey were reacted for 3 hours
  5. temperatureheated
  6. temperatureunder reflux for 6 hours
  7. customThe mixture thus obtained
  8. extractionextracted with benzene
  9. extractionThe benzene extract
  10. washwas washed successively with an aqueous solution of sodium hydrogencarbonate and water
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off
  13. additionHexane was added to the residue, and 3-(4-methylphenyl)-5-butyrylisoxazole
  14. customprecipitated as crystals
  15. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1700c3ba0d2d4d01bc4cf488654a426c
Quelldatensatz
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05602160

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