Sulfuric Acid → HCID 19927034, compound

HRID 1647330Notes

Reaction equation

HRID 1647330 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3([CH3:16])[C:7]([CH:8]=[C:9]([C:17]([O:19]C)=[O:18])[CH2:10][CH2:11]3)=[CH:6][CH2:5][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(=O)(=O)(O)O>CO.O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3([CH3:16])[C:7]([CH:8]=[C:9]([C:17]([OH:19])=[O:18])[CH2:10][CH2:11]3)=[CH:6][CH2:5][C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 56978353HCID 56978353, compound

Product 1

HCID 19927034HCID 19927034, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred solution of methyl (-)-2-chloro-4b-methyl-4b,5,6,10-tetrahydrophenanthrene-7-carboxylate (500 mg, 1.73 mmol.) in methanol (19 mL) and water (2 mL) was added potassium carbonate (300 mg). The solution was heated to reflux for 10 hours. The solution was allowed to cool to ambient temperature, was diluted with chloroform (100 mL) and was acidified with 1N sulfuric acid. The aqueous phase was further extracted with chloroform and the combined organic phases were dried over anhydrous magnesium sulfate. Removal of solvent under reduced pressure afforded crude acid as a yellow glass. The compound was purified by chromatography on silica (eluting with 25% ethyl acetate, 1% acetic acid in hexanes) to afford the title compound (396 mg) as a yellow crystalline solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 10 hours
  3. extractionThe aqueous phase was further extracted with chloroform
  4. dry with materialthe combined organic phases were dried over anhydrous magnesium sulfate
  5. customRemoval of solvent under reduced pressure
  6. customafforded crude acid as a yellow glass
  7. customThe compound was purified by chromatography on silica (eluting with 25% ethyl acetate, 1% acetic acid in hexanes)

Sources & evidence

ORD record
ord-ce4bfabf12914ebbb5dc4394ea7e1795
Source dataset
uspto-grants-1995_07
Patent number
US05430157

Reaction notes

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