Uses
3-Hydroxy-1-adamantyl methanol can be used to introduce adamantyl groups into the structure of target organic molecules. In organic synthesis methodology, it is mainly used for the structural modification and synthesis of sterically hindered organic ligands.
Chemical Properties
White solid
Synthesis
General procedure for the synthesis of 3-hydroxy-1-adamantanemethanol and 3-hydroxyadamantane from 1-adamantanemethanol: Under vigorous stirring, adamantan-1-ylmethanol (1a-1d) was added in batches over a period of 5-10 minutes to 15-20°C fuming nitric acid. The resulting solution was stirred vigorously for 1 h at 20°C and poured into 500 g of crushed ice. The product was extracted with butan-1-ol (6 mL), the organic layer was separated, 20 mL of hydrazine hydrate was added and the mixture was refluxed for 3 hours. After cooling, the mixture was diluted with 10 mL of butan-1-ol and washed sequentially with water (2 x 20 mL), 5% aqueous potassium hydroxide (3 x 15 mL) and water (2 x 10 mL). The organic phase was dried and evaporated under reduced pressure and the residue was recrystallized from toluene. The basic washings were acidified with aqueous HCl and the precipitated 3-hydroxyadamantane-1-carboxylic acid (5a-5d) was filtered. (3-Hydroxyadamantan-1-yl)methanol (4a) was synthesized from 2 g (0.012 mol) of 1a and 20 mL of fuming nitric acid in a yield of 1.6 g (75%) with a melting point of 140-142°C; literature value [50]: melting point 139-141°C. 3-Hydroxyadamantane-1-carboxylic acid (5a) was synthesized in a yield of 0.18 g (8%) with a melting point 203-205°C; literature value [64]: melting point 202-203 °C.
References
[1] Russian Journal of Organic Chemistry, 2018, vol. 54, # 9, p. 1294 - 1300
[2] Zh. Org. Khim., 2018, vol. 54, # 9, p. 1283 - 1289,8
