Sulfuric Acid → 1-Hydroxyadamantan-2-one

HRID 1977078Notes

Reaction equation

HRID 1977078 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11]N1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2C1=O.S(=O)(=O)(O)[OH:24]>C(O)(=O)C>[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.[OH:24][C:15]12[CH2:14][CH:21]3[CH2:20][CH:19]([CH2:10][CH:1]([CH2:2]3)[C:16]1=[O:17])[CH2:18]2

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 2

HCID 64151AdamantanoneYield 25%HCID 109648841-Hydroxyadamantan-2-oneYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 25 ml of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide, 0.05 mmol of 98% by weight sulfuric acid and 0.05 mmol of acetylacetonatovanadium V(AA)3, and the resultant mixture (pH 1.7) was stirred under an oxygen atmosphere at a temperature of 75° C. for 6 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, adamantane was converted into adamantanone (yield 25%) and 1-hydroxyadamantanone (yield 29%) with a conversion of 96%. Incidentally, excepting the above, 1-adamantanol (yield 10%), 1,3-adamantanediol (yield 12%) and other products (polyketone such as adamantanedione) (yield 20%) were formed.

Sources & evidence

ORD record
ord-3f70ffc1c46b498b875270c7ac53026d
Source dataset
uspto-grants-2001_05
Patent number
US06232258B1

Reaction notes

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