4-Chlorobenzoyl chloride → 4-(4-Chlorobenzamido)-phenylacetic acid

HRID 1277660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277660
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1>[OH-].[Na+].CC(C)=O.O>[Cl:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=2)=[O:18])=[CH:15][CH:14]=1

Komponenten

6

Edukt 2

HCID 85014-Chlorobenzoyl chlorideHCID 145334-Aminophenylacetic acid

Produkt 1

HCID 33670874-(4-Chlorobenzamido)-phenylacetic acidAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

7.6 g 4-Aminophenylacetic acid are dissolved in 50 ml 2 N aqueous sodium hydroxide solution and 50 ml acetone. A solution of 8.8 g 4-chlorobenzoyl chloride in 10 ml acetone is added dropwise thereto at 0° C. The reaction mixture is further stirred for 3 hours at ambient temperature, then diluted with water, filtered and the filtrate acidified with dilute hydrochloric acid. The precipitate obtained is reprecipitated via its sodium salt and recrystallized from ethanol. There are obtained 4.2 g (29% of theory) 4-(4-chlorobenzamido)-phenylacetic acid; m.p. 252° C.

Aufarbeitung

  1. customat 0° C
  2. filtrationfiltered
  3. customThe precipitate obtained
  4. customis reprecipitated via its sodium salt
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-fe180ee47f264eed9baca6fcd913e0f5
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04278680

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