38584-37-1

770-71-8

38584-37-1

42711-75-1

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.