Nitric Acid → Idramantone

HRID 234749Notes

Reaction equation

HRID 234749 reaction equation
[N+]([O-])(O)=O.[CH:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[C:6]1=[O:15])[CH2:12]2.[OH-:16].[Na+]>OS(O)(=O)=O>[OH:16][C:11]12[CH2:13][CH:7]3[CH2:8][CH:9]([CH2:14][CH:5]([C:6]3=[O:15])[CH2:12]1)[CH2:10]2

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 64151Adamantanone

Product 1

HCID 64184Idramantone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of H2SO4 (96%; 150 ml) and HNO3 (70%; 15 ml), cooled to 0° C. is added tricyclo[3.3.1.13,7 ]decan-2-one (10 g; 0.067 mole) and the mixture stirred at room temperature for 5 hrs. The reaction mixture is then poured over ice, basified to pH 8 using 50% NaOH, extracted into ether, dried over MgSO4 and evaporated to dryness. The resultant product is recrystallized from carbon tetrachloride to obtain 5-hydroxytricyclo[3.3.1.13,7 ]decan-2-one [(m. p. 314° C. (dec.)] which is used directly in step B.

Workup

  1. additionThe reaction mixture is then poured over ice
  2. extractionextracted into ether
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe resultant product is recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-4dcc6d7b7c474c5ab71c55198a5b4788
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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