Hydrochloric Acid → HCID 178444277, Verbindung

HRID 247529

Reaktionsgleichung

Reaktionsgleichung von HRID 247529
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:28][CH2:27]4)=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8](Cl)=[O:9].[Cl:37][C:38]1[CH:39]=[C:40]([OH:47])[CH:41]=[CH:42][C:43]=1[N+:44]([O-:46])=[O:45].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:21]=[CH:22][C:23]([C@H:26]4[CH2:31][CH2:30][C@H:29]([CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:28][CH2:27]4)=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]([O:47][C:40]1[CH:41]=[CH:42][C:43]([N+:44]([O-:46])=[O:45])=[C:38]([Cl:37])[CH:39]=1)=[O:9]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 102833-Chloro-4-nitrophenolHCID 178444276HCID 178444276, Verbindung

Produkt 1

HCID 178444277HCID 178444277, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The crude 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid 3-chloro-4-(chlorocarbonyl)phenyl ester obtained was dissolved in 150 ml of benzene and then added dropwise to a solution of 1.2 g of 3-chloro-4-nitrophenol in 110 ml of dry pyridine. The mixture was stirred at 65° C. overnight, then poured into a mixture of 500 ml of ice-water and 100 ml of concentrated hydrochloric acid and extracted with diethyl ether. The extract was washed three times with 100 ml of 3N hydrochloric acid each time and three times with 200 ml of water each time, then dried and evaporated. The crude 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-nitrophenoxy)carbonyl]phenyl ester obtained was chromatographed on silica gel with toluene/acetone (volume ratio 19:1). The fractions which were almost pure according to thin-layer chromatography (2.8 g) were recrystallized twice from ethyl acetate; m.p. (C-N) 132° C., cl.p. >250° C. (decomposition).

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe extract was washed three times with 100 ml of 3N hydrochloric acid each time and three times with 200 ml of water each time
  3. customdried
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2681b2e555344b4f95857442aee4ed08
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04708441

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