- Purification of 1-Adamantane carboxylic acid
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Possible impurities are trimethylacetic acid and C9 and C13 acids. Dissolve 15g of acid in CCl4 (300mL) and shake with 110 mL of 15N aqueous NH3 and the ammonium salt separates and is collected. Acid impurities form soluble ammonium salts. The salt is washed with cold Me2CO (20mL) and suspended in H2O (250mL). This is treated with 12N HCl and extracted with CHCl3 (100mL). The dried (Na2SO4) is evaporated and the residue recrystd from a mixture of MeOH (30mL) and H2O (ca 10mL) to give the pure acid (10-11g). Also recrystd from absolute EtOH and dried under vacuum at 100 °C.
Alternatively, the 1- carboxylic acid (CAS NO. ) (5g) is refluxed for 2h with 15mL of MeOH and 2mL of 98 % H2SO4 (cool when mixing this soln). Pour into 10 volumes of H2O and extract with the minimum volume of CHCl3 to give clear separation of phases. The extract is washed with H2O and dried (CaCl2) and distd. The is collected at 77-79 °C/lmm, m 38-39 °C. The ester is hydrolysed with the calculated amount of N KOH and refluxed until clear. Acidification with HCl provides the pure acid with 90% recovery. The amide crysts from cyclohexane, m 189 °C.
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