StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Tetrachlorophthalic anhydride → 2,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acid

HRID 27016
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 27016
[Cl:1][C:2]1[C:3]([Cl:15])=[C:4]([Cl:14])[C:5]([Cl:13])=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]=12.[CH2:16]([N:18]([CH2:26][CH3:27])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[CH:20]=1)[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[CH3:25][C:21]1[CH:20]=[C:19]([N:18]([CH2:16][CH3:17])[CH2:26][CH3:27])[CH:24]=[CH:23][C:22]=1[C:11]([C:6]1[C:5]([Cl:13])=[C:4]([Cl:14])[C:3]([Cl:15])=[C:2]([Cl:1])[C:7]=1[C:8]([OH:10])=[O:9])=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8326Tetrachlorophthalic anhydrideHCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 1043362,3,4,5-Tetrachloro-6-[4-(diethylamino)-2-methylbenzoyl]benzoic acidAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

A mixture of tetrachlorophthalic anhydride (21.4 g.), N,N-diethyl-m-toluidine (41 g.), aluminum chloride (30 g.) and o-dichlorobenzene (90 ml.) was heated (75°-95° C.) during one to two hours, then diluted with ice-water. The o-dichlorobenzene layer was separated and steam distilled. The residue was heated with dilute sulfuric acid. The mixture was poured onto ice and made alkaline. The resulting oil was heated in concentrated sulfuric acid. Dilution with water and purification of the product with toluene and hexane afforded 2-(2-methyl-4-(diethylamino)benzoyl)-3,4,5,6-tetrachlorobenzoic acid (IV: Y2 =CH3, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =Cl) (26 g., m.p. 117° C. with sublimation).

Aufarbeitung

  1. temperaturewas heated (75°-95° C.) during one to two hours
  2. customThe o-dichlorobenzene layer was separated
  3. distillationsteam distilled
  4. temperatureThe residue was heated with dilute sulfuric acid
  5. additionThe mixture was poured onto ice
  6. temperatureThe resulting oil was heated in concentrated sulfuric acid
  7. customDilution with water and purification of the product with toluene and hexane

Quellen und Nachweise

ORD-Eintrag
ord-bc1b787f42e34035a981fe1e10eb945e
Quelldatensatz
uspto-grants-1980_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04220357

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion