8-Methoxypsoralen → Xanthotoxol

HRID 22154

Reaktionsgleichung

Reaktionsgleichung von HRID 22154
[Mg].C[O:3][C:4]1[C:12]2[O:13][C:14]([CH:16]=[CH:17][C:11]=2[CH:10]=[C:6]2[CH:7]=[CH:8][O:9][C:5]=12)=[O:15]>C1C=CC=CC=1>[CH:7]1[C:6]2=[CH:10][C:11]3[CH:17]=[CH:16][C:14](=[O:15])[O:13][C:12]=3[C:4]([OH:3])=[C:5]2[O:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 41148-MethoxypsoralenHCID 5462224Magnesium

Produkt 1

HCID 65090Xanthotoxol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
165 °C

Versuchsvorschrift

To a suspension of magnesium (0.97 g, 0.04 mol) in dry benzene (75 ml) iodine (10.2 g, 0.04 mol) was added over a period of 1 hour. Then 75 ml of dry benzene was added and the mixture was refluxed for 1 hour. The next day, 8-methoxypsoralen (Sigma Cat. No. M 3501) (4.3 g, 0.02 mol) was added, and after stirring for 15 minutes, the solvent was evaporated under vacuum at 120° C. until the residue was practically dry. It was then further heated at 165° C. for 2 hours. The resulting solid was decomposed with dilute sulphuric acid and filtered. The solid was washed with water, suspended in dilute bisulfite solution, filtered again, washed with water and finally crystallized from dioxane and yielded colourless crystals (3.75 g), m.p. 246° C.

Aufarbeitung

  1. additionwas added over a period of 1 hour
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionM 3501) (4.3 g, 0.02 mol) was added
  4. customthe solvent was evaporated under vacuum at 120° C. until the residue
  5. customwas practically dry
  6. filtrationfiltered
  7. washThe solid was washed with water
  8. filtrationfiltered again
  9. washwashed with water
  10. customfinally crystallized from dioxane

Quellen und Nachweise

ORD-Eintrag
ord-ab8c2ceb59344aff92d6e5363ae5bf68
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05427779

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