Acetic Acid → 2-(4-Methoxy-3,5-dimethylphenyl)-3-methylindole

HRID 2309403

Reaktionsgleichung

Reaktionsgleichung von HRID 2309403
[CH3:1][C:2]1[CH:7]=[C:6]([C:8](=O)[CH2:9][CH3:10])[CH:5]=[C:4]([CH3:12])[C:3]=1[O:13][CH3:14].[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.Cl>C(O)C.O>[CH3:14][O:13][C:3]1[C:4]([CH3:12])=[CH:5][C:6]([C:8]2[NH:21][C:15]3[C:20]([C:9]=2[CH3:10])=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:7][C:2]=1[CH3:1]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 7516PhenylhydrazineHCID 129634181-(4-Methoxy-3,5-dimethylphenyl)propan-1-one

Produkt 1

HCID 136701412-(4-Methoxy-3,5-dimethylphenyl)-3-methylindoleAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

5.0 g of 2,6-dimethyl-4-propionylanisole and 2.8 g of phenylhydrazine were dissolved in 30 ml of ethanol. A small amount of acetic acid was added under reflux for 30 minutes. After cooling, 10 ml of a 20% ethanol solution of hydrogen chloride was added to the reaction mixture, and the mixture was refluxed for 1.5 hours. The reaction mixture was cooled, poured into water, extracted with benzene, washed with water, and dried. The solvent was evaporated, and the residue was crystallized from benzene-hexane to give 4.3 g of 2-(4-methoxy-3,5-dimethylphenyl)-3-methylindole.

Aufarbeitung

  1. temperatureunder reflux for 30 minutes
  2. temperatureAfter cooling
  3. temperaturethe mixture was refluxed for 1.5 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with benzene
  6. washwashed with water
  7. customdried
  8. customThe solvent was evaporated
  9. customthe residue was crystallized from benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-5d813c2174c94bf3b27f28f1e5f7ede2
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04695581

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