2-hydroxy-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one → 8-Methoxypsoralen

HRID 1448519Notes

Reaction equation

HRID 1448519 reaction equation
O[CH:2]1[O:17][C:5]2=[C:6]([O:15][CH3:16])[C:7]3[O:12][C:11](=[O:13])[CH:10]=[CH:9][C:8]=3[CH:14]=[C:4]2[CH2:3]1>C(O)=O>[CH3:16][O:15][C:6]1[C:7]2[O:12][C:11]([CH:10]=[CH:9][C:8]=2[CH:14]=[C:4]2[CH:3]=[CH:2][O:17][C:5]=12)=[O:13]

Participants

3

Reactant 1

HCID 203802212-hydroxy-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one

Product 1

HCID 41148-Methoxypsoralen

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 52.2 g. (0.223 mole) of crude 2-hydroxy-9-methoxy-2,3-dihydro-7H-furo[3,2-g][1]benzopyran-7-one in 900 ml of 98% formic acid was heated under argon at 100° for 45 min. The solvent was removed in vacuo and the dark residue crystallized. After drying on the high vac, the crude product, was taken up in the minimum amount of warm methylene chloride and filtered through an alumina column. Evaporation of fractions afforded pure methoxsalen, mp 145°-146°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe dark residue crystallized
  3. customAfter drying on the high vac
  4. filtrationfiltered through an alumina column
  5. customEvaporation of fractions

Sources & evidence

ORD record
ord-981b77c9f618459599ffe3a555a00409
Source dataset
uspto-grants-1979_12
Patent number
US04180659

Reaction notes

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