Iodine → Bergaptol

HRID 501891

Reaction equation

HRID 501891 reaction equation
II.[Mg].[I-].[Mg+2].[I-].C[O:8][C:9]1[C:17]2[CH:18]=[CH:19][C:20]([O:22][C:16]=2[CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][O:13]2)=[O:21]>CCOCC>[CH:11]1[C:10]2=[C:9]([OH:8])[C:17]3[CH:18]=[CH:19][C:20](=[O:21])[O:22][C:16]=3[CH:15]=[C:14]2[O:13][CH:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 2355BergaptenHCID 5462224MagnesiumHCID 5462737Magnesium diiodide

Product 1

HCID 5280371Bergaptol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of iodine (1.0 g, 4 mmol) and magnesium (0.2 g, 8 mmol) was stirred in anhydrous ether (30 ml) under reflux until colourless to prepare magnesium iodide. Bergapten (1.0 g, 4.5 mmol) was suspended in anhydrous ether and added to the solution. After heating the mixture to reflux for 45 min, the solvent was removed under reduced pressure. The residue was dried at 120° C. for 30 min, kept at 160-165° C. for 90 min, and decomposed with 25% sulfuric acid. The crude product was filtered, washed with a solution of thiosulfate, dried, and used for the synthesis of the 5-phenylalkoxy- and 5-cyclohexylalkoxypsoralens without further purification.

Workup

  1. temperatureunder reflux until colourless
  2. additionadded to the solution
  3. temperatureAfter heating the mixture
  4. temperatureto reflux for 45 min
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was dried at 120° C. for 30 min
  7. filtrationThe crude product was filtered
  8. washwashed with a solution of thiosulfate
  9. customdried
  10. customused for the synthesis of the 5-phenylalkoxy- and 5-cyclohexylalkoxypsoralens without further purification

Sources & evidence

ORD record
ord-6369b6afb54b4e3e8d7ac6854dc44961
Source dataset
uspto-grants-2010_08
Patent number
US07772408B1

Linked notes

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