Oxygen → 1,3,5-Adamantanetriol

HRID 1978114Notes

Reaction equation

HRID 1978114 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.[O:13]=O>C(O)(=O)C>[C:5]12([OH:13])[CH2:10][C:1]3([OH:12])[CH2:8][CH:7]([CH2:9][C:3]([OH:11])([CH2:2]3)[CH2:4]1)[CH2:6]2

Participants

4

Reactant 2

HCID 977OxygenHCID 5738291,3-Adamantanediol2×

Product 1

HCID 98990221,3,5-AdamantanetriolYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 25 ml of acetic acid were added 10 mmol of 1,3-adamantanediol, 1 mmol of NHPI and 0.05 mmol of acetylacetonatovanadium (III) (V(AA)3), and the resultant mixture was stirred in an oxygen atmosphere at a temperature of 75° C. for 6 hours. And, as a result, the 1,3-adamantanediol was converted into a 1,3,5-adamantanetriol (yield: 80%) with a conversion of 99%.

Sources & evidence

ORD record
ord-ed7264f61ce042258412dc654af36d0e
Source dataset
uspto-grants-2001_05
Patent number
US06235851B1

Reaction notes

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