Acetic Acid → 1,3-Adamantanediol

HRID 1602064Notes

Reaction equation

HRID 1602064 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]>>[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:23]12([OH:26])[CH2:24][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

6

Reactant 3

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

Product 3

HCID 64151AdamantanoneYield 6%HCID 641521-AdamantanolYield 39%HCID 5738291,3-AdamantanediolYield 49%

Procedure

To 25 ml of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide and a binary co-catalyst [0.1 mmol of acetylacetonatocobalt Co(AA)3 and 0.4 mmol of acetylacetonatoiron Fe(AA)3 ]and the resultant mixture 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 1-adamantanol (yield 39%) , 1,3-adamantanediol (yield 49%) and adamantanone (yield 6%) with a conversion of 99%.

Sources & evidence

ORD record
ord-5300959e4d8948eaa6388e6bd076c7a0
Source dataset
uspto-grants-1999_11
Patent number
US05981420

Reaction notes

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