Sulfuric Acid → Bicyclo[2.2.1]heptan-2-ol, 1-methyl-

HRID 2211328Notes

Reaction equation

HRID 2211328 reaction equation
C([O:4][CH:5]1[CH2:10][CH:9]2[CH2:11][C:6]1([CH3:12])[CH2:7][CH2:8]2)(=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>C(OCC)C>[CH3:12][C:6]12[CH2:11][CH:9]([CH2:8][CH2:7]1)[CH2:10][CH:5]2[OH:4]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 572634HCID 572634, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 557239Bicyclo[2.2.1]heptan-2-ol, 1-methyl-Yield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

290.0 g (1.73M) of the acetate (III) obtained in 1-2) above dissolved in 300 ml of absolute diethyl ether was added to 65.2 g (1.7M) of lithium aluminum hydride suspended in 800 ml of absolute diethyl ether at room temperature under a nitrogen gas stream. Then the resulting mixture was heated under reflux for six hours and stirred at room temperature over night. Subsequently 500 ml of a 5% aqueous solution of sulfuric acid was slowly added to the reaction mixture with stirring under ice-cooling. The ether phase was collected and dried over anhydrous magnesium sulfate. After evaporation of the ether, the residue was distilled under reduced pressure to give 209 g (theoretical yield: 96%) of the aimed compound (IV) as a colorless oily material. b.p.: 83° C./20 mmHg.

Workup

  1. temperatureThen the resulting mixture was heated
  2. temperatureunder reflux for six hours
  3. stirringwith stirring under ice-
  4. temperaturecooling
  5. customThe ether phase was collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter evaporation of the ether
  8. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-fc3b6599d3a8435a9f5296421db32b0a
Source dataset
uspto-grants-1995_10
Patent number
US05463118

Reaction notes

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