Acetone → 2,4-Dimethoxy-4b,5,6,8,8a-hexahydro-9(10H)-phenanthrone

HRID 1283866Notes

Reaction equation

HRID 1283866 reaction equation
[OH:1][C:2]1[CH:15]=[C:14](O)[C:13]2[CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)C(=O)[CH2:5][C:4]=2[CH:3]=1.S([O:23][CH3:24])(OC)(=O)=O.[C:25](=[O:28])([O-])[O-].[K+].[K+].[CH3:31]C(C)=O>O>[CH3:31][O:1][C:2]1[CH:15]=[C:14]([O:28][CH3:25])[C:13]2[CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)[C:24](=[O:23])[CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 203227742,4-Dihydroxy-4b,6,7,8,8a,10-hexahydrophenanthren-9(5H)-one

Product 1

HCID 50483822,4-Dimethoxy-4b,5,6,8,8a-hexahydro-9(10H)-phenanthrone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a flask equipped with a stirrer, dropping funnel, condenser, and gas inlet tube maintained under a nitrogen atmosphere, there is added 23.2 g (0.1 mole) of 2,4-dihydroxy-4b,5,6,7,8,8a,9,10-octahydro-9-oxo-phenanthrene, 20 g (0.15 mole) of dimethyl sulfate, 22 g (0.16 mole) of dry potassium carbonate and 500 ml of dry acetone, the resulting mixture is then refluxed with stirring overnight. The resulting suspension is cooled, 5 ml. of water is added and stirring is continued for an additional 5 minutes. The mixture is filtered, and the filtrate is concentrated to dryness. The resulting residue is recrystallized from acetone/methanol to give 2,4-dimethoxy-4b,5,6,7,8,8a,9,10-octahydro-9oxo-phenanthrene, m.p. 130°-131°C.

Workup

  1. customTo a flask equipped with a stirrer
  2. temperaturemaintained under a nitrogen atmosphere
  3. temperaturethe resulting mixture is then refluxed
  4. temperatureThe resulting suspension is cooled
  5. stirringstirring
  6. waitis continued for an additional 5 minutes
  7. filtrationThe mixture is filtered
  8. concentrationthe filtrate is concentrated to dryness
  9. customThe resulting residue is recrystallized from acetone/methanol

Sources & evidence

ORD record
ord-acfff7ef65e4451da4c5b83bcd055721
Source dataset
uspto-grants-1976_08
Patent number
US03976684

Reaction notes

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