Hydrochloric Acid → Pyridinium, 1-(2-hydroxy-3-(4-(4-nitrobenzoyl)phenoxy)propyl)-4-phenyl-, chloride

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Reaktionsgleichung

[O:1]1[CH2:22][CH:2]1[CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[C:23]1([C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[ClH:35]>O1CCOCC1.O>[Cl-:35].[OH:1][CH:2]([CH2:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)[CH2:22][N+:32]1[CH:33]=[CH:34][C:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:30][CH:31]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

A solution of 2.06 g (6.88 mmol) of 4-(2,3-epoxypropoxy)-4'-nitrobenzophenone in 50 ml of dioxan and 25 ml of water was treated with 1.06 g (6.88 mmol) of 4-phenylpyridine and stirred at 70° C. while adding 1N HCl at a pH less than 8. After stirring at 70° C. for 18 hours the mixture was cooled to 20° C., treated with 300 ml of water and extracted three times with 200 ml of chloroform. The organic phase was dried and concentrated. The residue was recrystallized from acetone. There was obtained 1-[2-hydroxy-3-[p-(p-nitrobenzoyl)phenoxy]propyl]-4-phenylpyridinium chloride in 50% yield, m.p. 240° C.

Aufarbeitung

stirringAfter stirring at 70° C. for 18 hours the mixture
temperaturewas cooled to 20° C.
extractionextracted three times with 200 ml of chloroform
customThe organic phase was dried
concentrationconcentrated
customThe residue was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag: ord-6282a2ceccf54c0594871507922c42f3
Quelldatensatz: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04675328

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