Sulfuric Acid → Diamantanone

HRID 2209407Notes

Reaction equation

HRID 2209407 reaction equation
[CH2:1]1[CH:6]2[CH:7]3[CH:13]4[CH2:14][CH:2]1[CH2:3][CH:4]1[CH:12]4[CH2:11][CH:9]([CH2:10][CH:5]12)[CH2:8]3.S(=O)(=O)(O)[OH:16]>>[CH2:1]1[CH:6]2[CH:5]3[CH:4]4[CH2:3][CH:2]1[CH2:14][CH:13]1[CH:12]4[C:11](=[O:16])[CH:9]([CH2:8][CH:7]12)[CH2:10]3

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 123154Congressane2×

Product 1

HCID 141569DiamantanoneYield 70%

Conditions

Temperature
75 °C

Procedure

The synthesis of 3-diamantanol (22) from diamantane follows Gund et al, J. Org. Chem., 39, 2987 (1974), incorporated herein by reference. To diamantane (2 g), prepared as in Example 3, Procedure 6, is added 96.6% sulfuric acid (100 ml); the reaction mixture is then heated for four hours at 75° C. with vigorous stirring. Stirring is continued at room temperature for one additional hour. The black reaction mixture is poured over ice and steam distilled. The steam distillate is extracted with ether, and the combined ether extracts are washed with water and dried over MgSO4. Evaporation of the solvent leaves 1.4 g (70% yield) of crude diamantanone. The product may be further purified by chromatography on alumina. The second fraction, eluted with benzene-ether (1:1) contains pure diamantanone (0.8 g, 37%). Recrystallization from petroleum ether gives white crystals, mp 249°-250° C.; IR (Nujol oil) 1745, 1720, 1295, 1245, 1045 cm-1.

Workup

  1. customis continued at room temperature for one additional hour
  2. customThe black reaction mixture
  3. additionis poured over ice and steam
  4. distillationdistilled
  5. extractionThe steam distillate is extracted with ether
  6. washthe combined ether extracts are washed with water
  7. dry with materialdried over MgSO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-40c825ab84274a6ab8c5820954b7923d
Source dataset
uspto-grants-1995_10
Patent number
US05455072

Reaction notes

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