Acetic Acid → 1,3-Adamantanediol

反応式

[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.[OH:12]N1C(=O)C2=CC=CC=C2C1=O.[C:24]([OH:27])(=O)[CH3:25]>>[C:3]12([OH:12])[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][C:1]([OH:11])([CH2:10]3)[CH2:2]1)[CH2:9]2.[C:24]12([OH:27])[CH2:25][C:1]3([OH:11])[CH2:8][CH:7]([CH2:9][C:3]([OH:12])([CH2:2]3)[CH2:4]1)[CH2:6]2

参加物

反応物 3

HCID 176Acetic Acid

HCID 10665N-Hydroxyphthalimide

HCID 641521-Adamantanol2 回

生成物 2

HCID 5738291,3-Adamantanediol収率 53%

HCID 98990221,3,5-Adamantanetriol収率 26%

実験手順

To 25 milliliters of acetic acid were added 1.52 grams (10 millimoles) of 1-adamantanol, 0.13 gram (0.8 millimole) of N-hydroxyphthalimide and 0.015 gram (0.06 millimole) of Co(AA)2, and the resultant mixture was stirred under an oxygen atmosphere at a temperature of 75° C. for three hours. As a result, 1-adamantanol was transformed, with a transformation rate of 80%, into 1,3-adamantanediol (selectivity for 1-adamantanol 66%, yield 53%) and 1,3,5-adamantanetriol (selectivity for 1-adamantanol 33%, yield 26%), with a selectivity for the alcohols of 99%.