Acetic Acid → 1-Carboxy-3,5,7-trihydroxyadamantane

HRID 1936526Notes

Reaction equation

HRID 1936526 reaction equation
[C:1]12([OH:13])[CH2:10][C:5]3([OH:11])[CH2:6][CH:7]([CH2:9][C:3]([OH:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.[C]=O.O=O.[C:18]([OH:21])(=[O:20])[CH3:19]>>[C:5]12([OH:11])[CH2:10][C:1]3([OH:13])[CH2:8][CH:7]([CH2:9][C:3]([OH:12])([CH2:2]3)[CH2:4]1)[CH2:6]2.[C:18]([C:19]12[CH2:9][C:3]3([OH:12])[CH2:2][C:1]([OH:13])([CH2:10][C:5]([OH:11])([CH2:4]3)[CH2:6]1)[CH2:8]2)([OH:21])=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 98990221,3,5-AdamantanetriolHCID 178418416HCID 178418416, compound

Product 2

HCID 98990221,3,5-AdamantanetriolHCID 120393761-Carboxy-3,5,7-trihydroxyadamantaneYield 80%

Conditions

Temperature
60 °C

Procedure

10 mmol of 1,3,5-adamantanetriol, 1 mmol of NHPI, 0.005 mmol of Co(AA)2 were added to 25 ml of acetic acid, and the mixture was stirred at 60° C. for 6 hours in a reactor with a gas pack inflated with a mixed gas (mixed gas: 2 L of carbon monoxide adn 0.5 L of oxygen; pressure: 5 kg/cm2) connected thereto. As a result, with a conversion of 1,3,5-adamantanetriol of 99%, there was obtained 1-carboxy-3,5,7-adamantanetriol (yield: 80%).

Sources & evidence

ORD record
ord-16e0740f99c8439180e1074c9a4183a8
Source dataset
uspto-grants-2002_05
Patent number
US06391520B1

Reaction notes

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