5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene and method for producing the same

A method for producing a 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene, comprising:

• a first step of forming a Mannich base by reacting a carbonyl compound and an amine compound with each other in an acidic solvent, to thereby obtain a reaction liquid comprising the Mannich base in the acidic solvent,
• the acidic solvent comprising a formaldehyde derivative and 0.01 mol/L or more of an acid represented by a formula:
• HX, wherein, in the formula, X represents one selected from the group consisting of F, Cl, Br, I, CH3COO, CF3COO, CH3SO3, CF3SO3, C6H5SO3, CH3C6H4SO3, HOSO3, and H2PO4,
• the carbonyl compound being represented by the following general formula (2):
• wherein in the formula (2), R2 and R3 each independently represent one selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 10 carbon atoms, and a fluorine atom, and n represents an integer of 0 to 12,
• the amine compound being represented by the following general formula (3):
• wherein in the formula (3), R4s each independently represent one selected from the group consisting of linear chain saturated hydrocarbon groups having 1 to 20 carbon atoms, branched chain saturated hydrocarbon groups having 3 to 20 carbon atoms, saturated cyclic hydrocarbon groups having 3 to 20 carbon atoms, and saturated hydrocarbon groups having a hydroxyl group and 1 to 10 carbon atoms, provided that the two R4s may be bonded to each other to form a ring selected from the group consisting of a pyrrolidine ring, a piperidine ring, a piperazine ring, and a morpholine ring, and X− represents one selected from the group consisting of F−, Cl−, Br−, I−, CH3COO−, CF3COO−, CH3SO3−, CF3SO3−, C6H5SO3−, CH3C6H4SO3−, HOSO3−, and H2PO4−,
• the Mannich base being represented by the following general formula (4):
• wherein R2, R3, and n in the formula (4) have the same meanings as those of R2, R3, and n in the formula (2), and R4s and X−s in the formula (4) have the same meanings as those of R4s and X− in the formula (3);
• and
• a second step of reacting the Mannich base and a diene compound with each other by adding an organic solvent, a base in an amount of 1.0 to 20.0 equivalents to the acid, and the diene compound to the reaction liquid, and then heating the reaction liquid, to thereby form a 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene,
• the diene compound being represented by the following general formula (5):
• wherein in the formula (5), R1 represents one selected from the group consisting of a hydrogen atom, alkyl groups having 1 to 10 carbon atoms, and a fluorine atom,
• the 5-norbornene-2-spiro-α-cycloalkanone-α′-spiro-2″-5″-norbornene being represented by the following general formula (1):
• wherein R1s in the formula (1) have the same meaning as that of R1 in the formula (5), and R2, R3, and n in the formula (1) have the same meanings as those of R2, R3, and n in the formula (2).