3,5-DIMETHYLADAMANTANE-1-CARBOXYLIC ACID

white to light yellow crystal powde

The same reaction apparatus as shown in was charged with 3, 5-dimethyl-1-adamantanol (purity: 99percent, 30.0 g), followed by addition of 96percent by mass concentrated sulfuric acid (208 g). After the mixture was stirred at room temperature and the starting material was confirmed to be dissolved, the flask was cooled to maintain the solution temperature within the range of 10° C. to 20° C. and formic acid (7.76 g) was added dropwise thereto over 30 minutes. After completion of the dropwise addition, the mixture was reacted at a reaction temperature of 35° C. for 3 hours. When the progress of the reaction was confirmed by GC, the conversion of 3, 5-dimethyl-adamantanol was found to be 100percent and 3, 5-dimethyl-1-adamantane carboxylic acid was generated in a reaction yield of 92.6percent. Subsequently, while cooling the flask again to maintain the solution temperature within the range of 10° C. to 20° C., 70percent nitric acid (19.6 g) was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was reacted at a reaction temperature of 50° C. for 5 hours. When the progress of the reaction was confirmed by GC, the conversion of 3, 5-dimethyl-1-adamantane carboxylic acid was found to be 100percent and 3-hydroxy-5, 7-dimethyladamantane-1-carboxylic acid was generated in a reaction yield of 98.0percent. (0052) The same purification apparatus as shown in was charged with sodium hydroxide (90.2 g), sodium sulfite (35.5 g) and ion exchanged water (812 g) to prepare a mixed solution of sodium hydroxide and sodium sulfite, followed by cooling the flask. To the above mixed solution, the reaction mixture containing 3-hydroxy-5, 7-dimethyladamantane-1-carboxylic acid was added while maintaining the solution temperature within the range of 10° C. to 40° C., and the precipitated crystals were collected by filtration and washed with water. The crystals were dried under reduced pressure at 40° C. for 8 hours to obtain white crystals of 3-hydroxy-5, 7-dimethyladamantane-1-carboxylic acid (32.6 g, yield: 87.5percent).

Molecular Weight:208.30
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:208.146329876
Monoisotopic Mass:208.146329876
Topological Polar Surface Area:37.3
Heavy Atom Count:15
Complexity:315
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes