Citric Acid → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

HRID 1534199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534199
[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([C:11](=O)[C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24].[OH-].[K+].NN.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(O)CO>[OH:1][C:2]1[C:7]2[C:8]([CH3:21])=[C:9]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:22][CH2:23][CH3:24]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 145797604-Hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran

Produkt 1

HCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuranAusbeute 58,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-2-(4-methoxybenzoyl)-3-methyl-5-propylbenzofuran (7.2 g; 22 mmoles), potassium hydroxide pellets (8.7 g; 155 mmoles), ethylene glycol (100 ml) and 99% hydrazine (3.0 ml) was heated with stirring and maintaining the internal temperature between 130° C. and 150° C. for 4 hours. The internal temperature was permitted to rise to 175° C. for 1 hour and excess water was always allowed to escape. The mixture was cooled and poured into excess 20% citric acid solution. The mixture was extracted with ether, washed with water, dried (Na2SO4), filtered, concentrated, and chromatographed to give 4 grams of the title compound.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturemaintaining the internal temperature between 130° C. and 150° C. for 4 hours
  3. temperatureThe mixture was cooled
  4. extractionThe mixture was extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-d172ec0f45d946e38584b438c4f087b9
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05087638

Notizen zur Reaktion

Wird geladen…