反应详情

温度

0 °C

Concentrated sulfuric acid (50 mL) and carbon tetrachloride (100 mL) were combined, cooled to 0° C. and vigorously stirred. Adamantan-2-ol (451 mg) was dissolved in 96% formic acid (6 mL) and the solution was added to the sulfuric acid over 1 hour. The reaction continued to stir at 0° C. for 90 min after which it was added to 300 mL of ice. The layers were separated and the aqueous layer was extracted with 50 mL carbon tetrachloride (2×). The organic layers were combined and extracted with 1N NaOH. The aqueous portion was extracted with methylene chloride (4×) then acidified with 5N HCl. The solution turned white and was cooled on ice. Filtration provided the desired adamantane-2-carboxylic acid (contaminated with about 5% adamantane-1-carboxylic acid) as a white powder.

1. stirringto stir at 0° C. for 90 min after which it
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with 50 mL carbon tetrachloride (2×)
4. extractionextracted with 1N NaOH
5. extractionThe aqueous portion was extracted with methylene chloride (4×)
6. temperaturewas cooled on ice
7. filtrationFiltration