Sulfuric Acid → 2-Hydroxytricyclo[3.3.1.13,7]decane-2-carbonitrile

HRID 745853Notes

Reaction equation

HRID 745853 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.S(=O)(=O)(O)O.[C-:17]#[N:18].[Na+].CCOCC>CO>[C:17]([C:2]1([OH:11])[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)#[N:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 64151Adamantanone

Product 1

HCID 34511512-Hydroxytricyclo[3.3.1.13,7]decane-2-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well stirred solution of 2-adamantanone (45.0 grams, 0.3 mol) in 200 ml methanol were added 50 ml concentrated sulfuric acid at a rate that caused the solution to reflux. Then a saturated aqueous solution of sodium cyanide (88.2 grams, 0.6 mol) was added, and the mixture was first refluxed for 1 hour and then stirred at room temperature for 3 additional hours. Ether was added, and the organic solution was decanted from the precipitated salts. The ether solution was washed with an aqueous solution of sodium chloride and water and then dried and evaporated to leave 43.0 grams (81%) of compound 4 as a beige crystalline solid, melting point >240° C. (decomposition).

Workup

  1. temperatureto reflux
  2. temperaturethe mixture was first refluxed for 1 hour
  3. customthe organic solution was decanted from the precipitated salts
  4. washThe ether solution was washed with an aqueous solution of sodium chloride and water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-6f3e91c38f514c1bb5876fbd2ae751b8
Source dataset
uspto-grants-1986_07
Patent number
US04600782

Reaction notes

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