Sodium Hydroxide → HCID 13338867, Verbindung

HRID 652459Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652459
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([O:19]CC)=[O:18])=[CH:15][C:14]=2[Br:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:23]=[CH:22][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[Br:24])=[C:6]([CH2:27][CH2:28][CH3:29])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 13338863Ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoate

Produkt 1

HCID 13338867HCID 13338867, VerbindungAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoate (1.50 g), ethanol (15 ml) and 1N sodium hydroxide (10 ml) was refluxed for 0.5 hour, then concentrated, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate, the solvent was distilled off, and the residue was chromatographed on a column of silica gel (50 g), and eluted with a solution of chloroform-acetone-formic acid (9:1:0.1). Recrystallization from ethyl acetate gave 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-bromobenzoic acid as colorless needles (1.06 g). Melting point 180°-182° C.

Aufarbeitung

  1. temperaturewas refluxed for 0.5 hour
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was chromatographed on a column of silica gel (50 g)
  8. washeluted with a solution of chloroform-acetone-formic acid (9:1:0.1)
  9. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-176ec672a9cd4b6c8d9d62ec13efb8bb
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04672073

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