8-Methoxypsoralen → Xanthotoxol

HRID 22154Notes

Reaction equation

HRID 22154 reaction equation
[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

Participants

4

Reactant 2

HCID 41148-MethoxypsoralenHCID 5462224Magnesium

Product 1

HCID 65090Xanthotoxol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
165 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ab8c2ceb59344aff92d6e5363ae5bf68
Source dataset
uspto-grants-1995_06
Patent number
US05427779

Reaction notes

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