[Na].[N:2](OCCC(C)C)=[O:3].O.[CH3:11][C@:12]12[C:20](=[O:21])[CH2:19][C@H:15]([C:16]1([CH3:18])[CH3:17])[CH2:14][CH2:13]2>C(OCC)C>[OH:3][N:2]=[C:19]1[CH:15]2[C:16]([CH3:17])([CH3:18])[C:12]([CH3:11])([CH2:13][CH2:14]2)[C:20]1=[O:21]In 600 ml of dried diethyl ether was dissolved 130 g (0.854 mol) of commercially available D-camphor, and 20.4 g of metallic sodium was added thereto. The solution was kept at 0° C. with stirring, and 123 ml (0.916 mol) of isoamyl nitrite was added thereto to conduct a reaction for 14 hours. After completion of the reaction, 200 ml of water was added to the reaction mixture, and the aqueous layer was separated. To the aqueous layer was added 400 ml of 10% hydrochloric acid, and the solid thus formed was extracted with diethyl ether. The ether layer was dried and concentrated to obtain 51 g of 3-hydroxyiminocamphor.
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