ChemicalBook CAS DataBase List 2-Adamantanol

2-Adamantanol synthesis

12synthesis methods

Product Name:2-Adamantanol
CAS Number:700-57-2
Molecular formula:C10H16O
Molecular Weight:152.23

Tricyclo[3.3.1.13,7]decane-2-carbonitrile, 2-hydroxy-

24779-92-8
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700-57-2
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28529-71-7
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Yield:700-57-2 92% ，28529-71-7 3%

Reaction Conditions:

with sodium tetrahydroborate;hydrogen;nickel dichloride in tert-butyl alcohol at 70; under 760.051 Torr; for 12 h;

Steps:

Hydrogenation of 2-hydroxy-2-cyanoadmantane 1l
Hydrogenation of 2-hydroxy-2-cyanoadmantane 1l was performed similarly, using sodium borohydride (0.6 g, 0.016 mol), 15 mL of tert-butanol, anhydrous nickel(II) chloride (1.0 g, 0.008 mol), and nitrile 1l (3.5 g, 0.02 mol). The reaction duration was 12 h, the temperature was 70°C. 2-Hydroxyadamantane 10l, content 92 wt %. Mass spectrum, m/e (I_rel, %): 152 [M] (8), 151 (80), 150 (100), 121 (6), 104 (11), 91.1 (17), 80.2 (14), 79 (5), 65 (4). 2-Hydroxy-2-aminomethyladamantane, content 3 wt %. Mass spectrum, m/e (I_rel, %): 182.9 (7.5) [M+2], 182.0 (44.5) [M+1], 181.0 (16.3) [M], 152.1 (2.6), 106.0 (7), 104.9 (100), 77.0 (70), 51.0 (37.7), 50.0 (24.7).

References:

Mokhov;Popov;Shcherbakova [Russian Journal of General Chemistry,2016,vol. 86,# 2,p. 273 - 280][Zh. Obshch. Khim.,2016,vol. 86,# 2,p. 245 - 252,8]

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