Water → 5,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

HRID 2051410Notes

Reaction equation

HRID 2051410 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]([O:16]C)=[C:11]2[C:3]=1[CH:4]1[CH:9]([C:10]2=[O:18])[CH2:8][CH2:7][CH2:6][CH2:5]1.[I-].[Na+].[Cl-].[Al+3].[Cl-].[Cl-].O>C(#N)C>[CH3:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]([OH:16])=[C:11]2[C:3]=1[CH:4]1[CH:9]([C:10]2=[O:18])[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6451240Aluminum(III) ChlorideHCID 140437135,7-Dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 151571835,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 Grams of 5,7-dimethyl-8-methoxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone was dissolved in 45 ml of acetonitrile and to the solution were gradually added 12.14 g of sodium iodide and 10.79 g of freshly ground aluminum chloride. After stirring at room temperature for 1.5 hour, the reaction mixture was poured into water and extracted with dichloromethane. The organic layer was dried with magnesium sulfate and then the solvent was distilled off. The residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20) and thereafter recrystallized from ethanol to obtain 9.34 g of 5,7-dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2b818100f38740609ed2e11609e0d449
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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