Acetic Acid → 1-Adamantanol

HRID 618994Notes

Reaction equation

HRID 618994 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.O=O.[C:25]([OH:28])(=O)[CH3:26]>>[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:25]12([OH:28])[CH2:26][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([OH:11])([CH2:8]3)[CH2:2]1)[CH2:4]2.[CH:15]12[CH2:14][CH:21]3[CH2:20][CH:19]([CH2:8][CH:1]([CH2:2]3)[C:16]1=[O:17])[CH2:18]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 977OxygenHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 3

HCID 64151AdamantanoneYield 7%HCID 641521-AdamantanolYield 42%HCID 5738291,3-AdamantanediolYield 31%

Procedure

To 25 milliliters of acetic acid were added 10 millimoles of adamantane, 1 millimole of N-hydroxyphthalimide and 0.05 millimole of zirconyl acetate ZrO(OAc)2. The resultant mixture was stirred at a temperature of 75° C. for 6 hours in an oxygen atmosphere. As a result, adamantane was transformed into 1-adamantanol (yield 42%), 1,3-adamantanediol (yield 31%) and 2-adamantanone (yield 7%) with a transformation rate of 91 percent.

Sources & evidence

ORD record
ord-09072ad13214402dba63228fb91df229
Source dataset
uspto-grants-1999_09
Patent number
US05958821

Reaction notes

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