Acetic Acid → Adamantanone

HRID 1977079Notes

Reaction equation

HRID 1977079 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.[C:23]([OH:26])(=O)[CH3:24]>>[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:26][C:23]12[CH2:24][CH:19]3[CH2:20][CH:21]([CH2:14][CH:15]([CH2:18]3)[C:16]1=[O:17])[CH2:1]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 2

HCID 64151AdamantanoneYield 32%HCID 109648841-Hydroxyadamantan-2-oneYield 16%

Procedure

To 25 ml of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide and 0.2 mmol of phosphovanadotungstic acid (PV4W8O40.30H2), and the resultant mixture (pH 1.9) 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 32%) and 1-hydroxyadamantanone (yield 16%) with a conversion of 79%. Incidentally, excepting the above, 1-adamantanol (yield 15%), 1,3-adamantanediol (yield 8%) and other products (polyketone such as adamantanedione) (yield 8%) were formed.

Sources & evidence

ORD record
ord-502beb28616c40f2868e31ecd5619db8
Source dataset
uspto-grants-2001_05
Patent number
US06232258B1

Reaction notes

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