[Cl-:1].[Na+].[C:3]12([CH2:13][C:14]([OH:16])=[O:15])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl.C(O)(C)(C)C>[C:14]([CH2:13][C:3]12[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][C:5]([Cl:1])([CH2:6]3)[CH2:4]1)[CH2:10]2)([OH:16])=[O:15]18 Grams of sodium chloride were added in about 20 equal portions to a mixture of 3 g of 1-adamantyl-acetic acid, 60 ml. of carbon tetrachloride and 200 g of 96% sulfuric acid which was kept at 5° -10°C by external cooling under thorough stirring over a period of 6 hours while a mixture of 9 g of t-butanol and 20 ml. of carbon tetrachloride was added thereto dropwise over 30 minutes. The reaction mixture was poured onto 300 g of broken ice pieces. The crystalline precipitate was filtered out, washed with water sufficiently and air-dried to obtain 3.2 g (yield: 91.1%) of crude 1-carboxymethyl-3-chloroadamantane.
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