Acetic Acid → 5-Methoxy-2,3,3-trimethyl-3H-indole

HRID 127152

Reaktionsgleichung

Reaktionsgleichung von HRID 127152
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH3:10][C:11](O)([C:13](=O)[CH3:14])[CH3:12].C(O)(=O)C.C1(C)C=CC=CC=1>O>[CH3:14][C:13]1[C:11]([CH3:12])([CH3:10])[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=2[N:9]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1140TolueneHCID 7732P-AnisidineHCID 82613-Hydroxy-3-methyl-2-butanone

Produkt 1

HCID 110953925-Methoxy-2,3,3-trimethyl-3H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

246 parts of p-anisidine, 204 parts of 2-methyl-2-hydroxy-butan-3-one and 10 parts of acetic acid in 650 parts of toluene are heated, with removal of water from the system, until no more water separates off. The solvent is then distilled off and the residue is heated for 5 hours at 220° C. After cooling to 160° C., 10 parts of concentrated sulfuric acid are added; the mixture is kept at 160° C. for 3 hours, whilst distilling off the water formed. Distillation under reduced pressure (21 mbar) gives 318.7 parts of 5-methoxy-2,3,3-trimethyl-indolenine (melting point 53°-54° C.), corresponding to 84.3% of theory.

Aufarbeitung

  1. distillationThe solvent is then distilled off
  2. temperatureAfter cooling to 160° C.
  3. addition10 parts of concentrated sulfuric acid are added
  4. distillationwhilst distilling off the water
  5. customformed
  6. distillationDistillation under reduced pressure (21 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-7f18f49789c24e61a207293027d2f17d
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04255333

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