Oxygen → 1-Adamantanol

HRID 1637067Notes

Reaction equation

HRID 1637067 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C12CC3CC(CC(C3)C1)C2.O=O.[OH:26]N1C(=O)C2=CC=CC=C2C1=O>>[C:9]12([OH:26])[CH2:8][CH:7]3[CH2:6][CH:11]([CH2:12][CH:13]([CH2:5]3)[CH2:1]1)[CH2:10]2.[C:1]1(=[O:26])[C:13]2[C:5]([C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 977OxygenHCID 6853FluoreneHCID 9238AdamantaneHCID 10665N-Hydroxyphthalimide

Product 2

HCID 641521-AdamantanolHCID 22281833Fluoreneone

Procedure

In page 762 of the "Lecture Draft II" (1994) of 67th Spring Annual Meeting of Chemical Society of Japan, it is reported that oxidation of an alcohol such as benzyl alcohol or benzhydrol with air using vanadomolybdophosphoriate and N-hydroxyphthalimide provides a ketone such as acetophenone or benzophenone in a high yield, and that oxidation of fluorene or adamantane with oxygen using N-hydroxyphthalimide gives a corresponding adamantanol or fluorenone.

Sources & evidence

ORD record
ord-7ca3d62deb444295a7f83ee2af8410dc
Source dataset
uspto-grants-2000_03
Patent number
US06037507

Reaction notes

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