Oxygen → 3-Hydroxyadamantane-1-carboxylic acid

HRID 1978110Notes

Reaction equation

HRID 1978110 reaction equation
[C:1]([C:4]12[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2)([OH:3])=[O:2].[O:14]=O>C(O)(=O)C>[C:1]([C:4]12[CH2:13][CH:8]3[CH2:7][CH:6]([CH2:12][C:10]([OH:14])([CH2:9]3)[CH2:11]1)[CH2:5]2)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 977OxygenHCID 132351-Adamantanecarboxylic acid2×

Product 1

HCID 27365183-Hydroxyadamantane-1-carboxylic acidYield 56%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 25 ml of acetic acid were added 10 mmol of 1-carboxyadamantane, 1 mmol of NHPI and 0.05 mmol of V (AA)3, and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 75° C. for 5 hours. And, as a result, the 1-carboxyadamantane was converted into a 1-carboxy-3-adamantanol (yield: 56%, white solid), a 1-carboxy-3,5-adamantanediol (yield:28%, light yellow solid), a 1-carboxy-4-adamantanone (yield: 4%) with a conversion of 99%.

Sources & evidence

ORD record
ord-3ef1fe48847143a5a125d641a79ea234
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

Loading…