Phthalic Anhydride → 2-(4-(Diethylamino)-2-methylbenzoyl)benzoic acid

HRID 27009

Reaktionsgleichung

Reaktionsgleichung von HRID 27009
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([N:14]([CH2:22][CH3:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)[CH3:13].[Cl-].[Al+3].[Cl-].[Cl-].ClC1C=CC=CC=1>O>[CH3:21][C:17]1[CH:16]=[C:15]([N:14]([CH2:12][CH3:13])[CH2:22][CH3:23])[CH:20]=[CH:19][C:18]=1[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5]

Komponenten

6

Edukt 4

HCID 6811Phthalic AnhydrideHCID 7964Chlorobenzene2×HCID 66679N,N-diethyl-m-toluidineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 1043352-(4-(Diethylamino)-2-methylbenzoyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of phthalic anhydride (60 g.), N,N-diethyl-m-toluidine (162.8 g.), aluminum chloride (120 g.) and chlorobenzene (360 ml.) was heated (75°-95° C.) during one and one-half hours, then diluted with water (200 ml., then more). More chlorobenzene (200 ml.) was added and the chlorobenzene layer was separated and steam distilled. Addition of sodium hydroxide solution (10%) to a solution of the residue in dilute sulfuric acid (20%, 250 ml.) afforded 2-(2-methyl-4-(diethylamino)benzoyl)benzoic acid (IV: Y2 =CH3, Y'4 =(CH3CH2)2N, Z4 =Z"5 =Z"6 =Z7 =H).

Aufarbeitung

  1. temperaturewas heated (75°-95° C.) during one and one-half hours
  2. customthe chlorobenzene layer was separated
  3. distillationsteam distilled
  4. additionAddition of sodium hydroxide solution (10%) to a solution of the residue in dilute sulfuric acid (20%, 250 ml.)

Quellen und Nachweise

ORD-Eintrag
ord-61d7ac485ebb41cead0d0ac85fed42d1
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220357

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