Thionyl Chloride → 5,7-dimethyl-8-methoxy-2,3,4,4a-tetrahydro-1H-fluorene

HRID 2051418Notes

Reaction equation

HRID 2051418 reaction equation
S(Cl)(Cl)=O.[CH3:5][C:6]1[CH:18]=[C:17]([CH3:19])[C:16]([O:20][CH3:21])=[C:15]2[C:7]=1[CH:8]1[CH:13]([CH:14]2O)[CH2:12][CH2:11][CH2:10][CH2:9]1>C(Cl)(Cl)Cl>[CH3:5][C:6]1[CH:18]=[C:17]([CH3:19])[C:16]([O:20][CH3:21])=[C:15]2[C:7]=1[CH:8]1[C:13](=[CH:14]2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 151571985,7-Dimethyl-8-methoxy-9-hydroxy-1,2,3,4,4a,9a-hexahydrofluorene

Product 1

HCID 151571995,7-dimethyl-8-methoxy-2,3,4,4a-tetrahydro-1H-fluoreneYield 88.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5.5 Milliliters of thionyl chloride was added dropwise to a chloroform solution containing 16.1 g of 5,7-dimethyl-8-methoxy-9-hydroxy-1,2,3,4,4a,9a-hexahydrofluorene under ice-cooling. After completion of the addition, reaction was effected at the same temperature for 2 hours. The reaction mixture was washed successively with water twice, saturated aqueous sodium chloride solution and saturated sodium bicarbonate solution and dried with magnesium sulfate. Then, the solvent was distilled off and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20) to obtain 13.26 g of 5,7-dimethyl-8-methoxy-2,3,4,4a-tetrahydro-1H-fluorene.

Workup

  1. temperaturecooling
  2. additionAfter completion of the addition, reaction
  3. washThe reaction mixture was washed successively with water twice
  4. dry with materialsaturated aqueous sodium chloride solution and saturated sodium bicarbonate solution and dried with magnesium sulfate
  5. distillationThen, the solvent was distilled off
  6. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate:n-hexane=1:20)

Sources & evidence

ORD record
ord-f909d27acca6427880be1584b841bb59
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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