Formic Acid → 2-Adamantanecarboxylic acid

반응식

S(=O)(=O)(O)O.C(Cl)(Cl)(Cl)Cl.[CH:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH:12]1O)[CH2:18]2.[CH:22]([OH:24])=[O:23]>>[CH:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH:12]1[C:22]([OH:24])=[O:23])[CH2:18]2

참가 물질

반응물 4

HCID 284Formic Acid

HCID 1118Sulfuric Acid2회

HCID 5943Carbon Tetrachloride

HCID 641492-Adamantanol

생성물 1

HCID 3038022-Adamantanecarboxylic acid수율 5%

반응 조건

온도: 0 °C

실험 절차

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.