Nitric Acid → 3-Hydroxyadamantane-1-carboxylic acid

HRID 2170260Notes

Reaction equation

HRID 2170260 reaction equation
[N+]([O-])(O)=O.[C:5]12([OH:15])[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH2:8]3)[CH2:6]1)[CH2:12]2.C12([C:26]([OH:28])=[O:27])CC3CC(CC(C3)C1)C2>>[OH:15][C:5]12[CH2:12][CH:11]3[CH2:10][CH:9]([CH2:8][C:7]([C:26]([OH:28])=[O:27])([CH2:13]3)[CH2:6]1)[CH2:14]2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 132351-Adamantanecarboxylic acid2×HCID 641521-Adamantanol

Product 1

HCID 27365183-Hydroxyadamantane-1-carboxylic acidYield 25.2%

Procedure

The same operations as conducted in Example 1 were repeated, except that the reaction mixture temperature after dropwise addition of nitric acid was set to 80° C. In the first carboxylation reaction step, the conversion of 1-adamantanol was found to be 99.0% and 1-adamantane carboxylic acid was generated in a reaction yield of 97%. In the second oxidation reaction step, the conversion of 1-adamantane carboxylic acid was found to be 98.0% and white crystals of 3-hydroxy adamantane-1-carboxylic acid (9.8 g, yield: 25.2%) were obtained.

Workup

  1. customwas set to 80° C
  2. customIn the first carboxylation reaction step
  3. customwas generated in a reaction yield of 97%
  4. customIn the second oxidation reaction step

Sources & evidence

ORD record
ord-3d7f983c596946d2a3f536f713f56c12
Source dataset
uspto-grants-2015_06
Patent number
US09051256B1

Reaction notes

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