Benzil → 2,5-Bis(4-methoxyphenyl)-3,4-diphenylcyclopenta-2,4-dien-1-one

HRID 380707

Reaktionsgleichung

Reaktionsgleichung von HRID 380707
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26](=[O:36])[CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:21][CH:20]=1.[OH-].[K+]>>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([C:27]2[C:26](=[O:36])[C:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:9]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:33][CH:32]=1

Komponenten

4

Edukt 3

HCID 8651BenzilHCID 14797Potassium HydroxideHCID 37909281,3-Bis(4-methoxyphenyl)propan-2-one

Produkt 1

HCID 2674342,5-Bis(4-methoxyphenyl)-3,4-diphenylcyclopenta-2,4-dien-1-oneAusbeute 91 %

Versuchsvorschrift

Equivalent weights of benzil and the 1,3-bis(4-methoxyphenyl)propanone prepared in the first step are dissolved in, for example, alcohol and heated to incipient boiling. A condensation reaction is initiated by the addition of a small amount of an aqueous potassium hydroxide solution. The solution is heated at reflux to form a purple-black slurry which on purification results in an excellent yield (91%) of purple-colored crystalline 2,5-bis (4-methoxyphenyl)-3,4-diphenylcyclopentadienone, or α,α′-bis(4-methoxy)-tetracyclone, melting at approximately 186-188° C.

Aufarbeitung

  1. temperatureheated to incipient boiling
  2. customA condensation reaction
  3. temperatureThe solution is heated
  4. temperatureat reflux
  5. customto form a purple-black slurry which
  6. customon purification
  7. customresults in

Quellen und Nachweise

ORD-Eintrag
ord-a4a62482f4534bacb7709b4ed59a4c6f
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303733B1

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