Acetic Acid → 4-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid

HRID 1980539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1980539
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17]([OH:20])(=[O:19])[CH3:18].C([O:24][C:25](=[O:27])C)(=O)C.P(=O)(O)(O)O>O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:3]2[CH2:11][CH2:12][C:18]([C:25]([OH:24])=[O:27])([C:17]([OH:20])=[O:19])[CH2:5][CH:4]=2)=[C:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1004Phosphoric AcidHCID 7918Acetic AnhydrideHCID 770951-Methyl-2-phenylindole

Produkt 1

HCID 134092844-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acidAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 9.0 g (0.043 mol) of 1-methyl-2-phenylindole, 9.3 g (0.05 mol) 4,4-cyclohexanonedicarboxylic acid, 100 mL of acetic acid, 4.7 mL of acetic anhydride, and 1 mL of 85% phosphoric acid was stirred at room temperature for 17 h, and then 100 mL of water was added dropwise to give a white solid which was collected and washed with water. The solid was taken up in ether, washed with water three times and with brine two times, dried over magnesium sulfate, concentrated in vacuo, and crystallized from acetonitrile to give 8.4 g (52%) of 4-(1methyl-2-phenyl-1H-indol-3-yl)-3-cyclohexene-1,1-dicarboxylic acid, m.p. 210°-211° C.

Aufarbeitung

  1. customto give a white solid which
  2. customwas collected
  3. washwashed with water
  4. washwashed with water three times and with brine two times
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customcrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a37511ea74ee4c9da4dee2d9b69eab44
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04510158

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