3-Phenylprop-2-Enal → 2,3,6-Triphenylcyclohexenone

HRID 5051

Reaktionsgleichung

Reaktionsgleichung von HRID 5051
[CH2:1]([C:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17](=O)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(NCC)C>C(O)C>[C:11]1([C:10]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:18][CH:17]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:8]=2[OH:9])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:11]1([C:10]2[C:8](=[O:9])[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:17][CH2:18][C:19]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 3073-Phenylprop-2-EnalHCID 75931,3-Diphenyl-2-propanoneHCID 8021Diethylamine

Produkt 2

HCID 124726242,3,6-TriphenylphenolHCID 544043612,3,6-TriphenylcyclohexenoneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2,3,6-Triphenylphenol was prepared according to A. S. Hay and R. F. Clark (Macromolecules, 3, 533, 1970). 11.36 g (54 mmoles) of dibenzylketone, 7.14 g (54 mmoles) of cinnamaldehyde and 5 mL of diethylamine were mixed and the solution became yellow and after 20 min. a yellow solid deposited. The solid was added to ethanol (80 mL), cooled and filtered to yield 2,3,6-triphenylcyclohexenone (91%). The product (8.0 g) was mixed with 1 g of 5% Pd on carbon and heated at 270° C. for 30 min and then cooled. The mixture was dissolved in hot ethylacetate and the hot solution was filtered and cooled to yield 2,3,6-triphenylphenol (69%). The oxidation of triphenylphenol (5 g) was carried out in butyronitrile (50 mL) with a CuCl catalyst (0.4 g) by passing oxygen through the stirred solution at 100° C. for 8 hours. The reaction mixture was cooled and filtered to yield (82%) of the crude biphenol. Reduction with a few drops of hydrazine in hot acetic acid reduced any of the diphenoquinone in the product to give 2,2',3,3',5,5'-hexaphenyl-[1,1'-biphenyl]-4,4'-diol which was further purified by crystallization.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5f1016e69d7f473b92e9112c6cc82462
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05243016

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