Hydrochloric Acid → 4'-Hexyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-cyanophenoxy)carbonyl]phenyl ester

HRID 247518

Reaktionsgleichung

Reaktionsgleichung von HRID 247518
[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12](=[O:31])[C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl:32][C:33]1[CH:34]=[C:35]([OH:41])[CH:36]=[CH:37][C:38]=1[C:39]#[N:40].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:12]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:24]=3)=[CH:15][CH:14]=2)=[O:31])[CH:8]=[CH:7][C:3]=1[C:4]([O:41][C:35]1[CH:36]=[CH:37][C:38]([C:39]#[N:40])=[C:33]([Cl:32])[CH:34]=1)=[O:5]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 5927972-Chloro-4-hydroxybenzonitrileHCID 201594972-Chloro-4-[[p-(p-hexylphenyl)benzoyl]oxy]benzoyl chloride

Produkt 1

HCID 538219254'-Hexyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-cyanophenoxy)carbonyl]phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The crude 2-chloro-4-{[p-(p-hexylphenyl)benzoyl]oxy}benzoyl chloride obtained was dissolved in 125 ml of benzene and then added dropwise to a solution of 4.0 g of 3-chloro-4-cyanophenol in 100 ml of pyridine. The mixture was stirred at a bath temperature of 65° C. overnight, then poured into ice-cold, dilute hydrochloric acid and extracted with diethyl ether. The extract was washed several times with 3N hydrochloric acid, then washed neutral with water, dried and evaporated. The crude 4'-hexyl-4-biphenylcarboxylic acid 3-chloro-4-[(3-chloro-4-cyanophenoxy)carbonyl]phenyl ester obtained was chromatographed on silica gel with toluene/dichloromethane (1:1). The fractions (8.2 g) which were practically pure according to thin-layer chromatography were recrystallized once from ethyl acetate and once from ethyl acetate and a small amount of hexane; m.p. (C-N) 95° C., cl.p. (N-I) 235° C.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe extract was washed several times with 3N hydrochloric acid
  3. washwashed neutral with water
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-25bfb25d4d0c46e59a7483fae39bf83b
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04708441

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