Acetic Acid → 4-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid

HRID 986708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986708
[C:1]([O:4][C:5]1[C:6]([CH2:28][CH2:29][CH3:30])=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:27])[CH3:26])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=1[Br:21])(=[O:3])[CH3:2].C(O)(=[O:33])C.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[C:1]([O:4][C:5]1[C:6]([CH2:28][CH2:29][CH3:30])=[C:7]([CH:22]=[CH:23][C:24]=1[C:25](=[O:27])[CH3:26])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]([OH:33])=[O:18])=[CH:15][C:14]=1[Br:21])(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 20157039HCID 20157039, Verbindung

Produkt 1

HCID 137456304-[3-(3-Acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-bromobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]3-bromobenzaldehyde (2.39 g) in acetone (50 ml) was added acetic acid (50 ml). To the well stirred mixture was added pulverized potassium permanganate (1.58 g) by portions at room temperature. The reaction was allowed to proceed while stirring for one hours. The reaction mixture was concentrated under reduced pressure, and the concentrate was subjected to extraction with chloroform. Insoluble materials were filtered off, and the filtrate was washed with a dilute aqueous solution of hydrogen peroxide, then with water. The resulting solution was dried and concentrated to give colorless and clear syrup. Crystallization from aqueous alcohol gave 4-[3-(3-acetoxy-4-acetyl-2 propylphenoxy)propoxy]-3-bromobenzoic acid (2.0 g), m.p. 155°-156° C.

Aufarbeitung

  1. additionwas added
  2. customat room temperature
  3. stirringwhile stirring for one hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. extractionthe concentrate was subjected to extraction with chloroform
  6. filtrationInsoluble materials were filtered off
  7. washthe filtrate was washed with a dilute aqueous solution of hydrogen peroxide
  8. customThe resulting solution was dried
  9. concentrationconcentrated
  10. customto give colorless
  11. customCrystallization from aqueous alcohol

Quellen und Nachweise

ORD-Eintrag
ord-cfaa9183f3f34940be5da01a2ec97ab9
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04714774

Notizen zur Reaktion

Wird geladen…