Formaldehyde → Dihydrobenzoxazine

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One mole of 3(4),8(9),-bis(aminomethyl)tricyclo[5,2,1,02,6]decane as saturated alicyclic hydrocarbon diamine compound having a condensed ring structure, two moles of phenol as the phenol compound represented by Formula (1), as well as, 4 moles of paraformaldehyde as aldehyde compound and 1500 g of chloroform were mixed. This mixture was heated to 60° C. under stirring, and the reaction was carried out for 6 hours since chloroform started circulating. After the end of the reaction, the reaction mixture was washed with an aqueous solution of 1 N sodium hydroxide, and then rinsed with ion exchanged water. Then, after the chloroform phase was dried with anhydrous sodium sulfate, chloroform was evaporated with a rotary evaporator to obtain a bifunctional dihydro benzoxazine compound in which R14 of Formula (2) is the amino residue of 3(4),8(9),-bis(aminomethyl)tricyclo[5,2,1,02,6]decane.

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