Novel spiro ring expansion monomer containing unsaturated bond and ester group and preparation method thereof
An expansion monomer and unsaturated technology, applied in the direction of organic chemistry, etc., can solve the problems of inability to polymerize the monomer, high storage requirements, unstable monomer, etc., and achieve the effect of good polymerization effect, few synthesis steps and easy operation.
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Embodiment 1
[0044] This embodiment discloses a novel spiro ring expansion monomer containing unsaturated bonds and ester groups. The structural formula of the novel spiro ring expansion monomer is as follows:
[0045]
[0046] Wherein, R is a group containing an unsaturated bond.
[0047] When R is a methyl vinyl group, the structural formula of the novel spiro ring expansion monomer is:
[0048]
[0049] When R is a vinyl group, the structural formula of the novel spiro ring expanded monomer is:
[0050]
[0051] When R is a p-fluorostyrene group, the structural formula of the novel spiro ring expansion monomer is:
[0052]
[0053] To prepare the above-mentioned novel spiro ring expanded monomer, firstly, a spiro ring intermediate (DHOM) must be synthesized, and then the spiro ring intermediate is subjected to an ester-forming reaction to obtain a novel spiro ring expanded monomer.
[0054] The structural formula of the spiro ring intermediate (DHOM) is:
[0055]
[00...
Embodiment 2
[0061] This example specifically discloses a method for preparing a spiro ring intermediate (DHOM).
[0062] At room temperature (25° C.), 100.2 g of trimethylolpropane (white solid), 1.88 g of p-toluenesulfonic acid monohydrate, and 290 mL of dichloromethane were sequentially added to a 1 L reaction flask. Weigh 75.1g of tetraethyl orthocarbonate and add it to the reaction flask. When the reaction solution is reacted at room temperature for 15 hours, then add 50mL of 15% ammonia water to the reaction solution, then add 180mL of purified water for washing and separation, and collect the organic layer. Concentrate the organic phase under reduced pressure to obtain a colorless viscous liquid, add 80 mL of petroleum ether, stir well, crystallize at room temperature (25° C.) for more than 10 h, and precipitate a white solid, which is filtered. The filter cake was rinsed with 80 mL of petroleum ether, dried, and weighed 62.0 g with a yield of 61.5% and a purity of 87% (GC).
Embodiment 3
[0064] This example specifically discloses another method for preparing a spirocyclic intermediate (DHOM).
[0065]At room temperature (25° C.), 100.2 g of trimethylolpropane (white solid), 1.88 g of p-toluenesulfonic acid monohydrate, and 290 mL of dichloromethane were sequentially added to a 1 L reaction flask. Then the temperature was lowered to 10-30° C., and 75.1 g of tetraethyl orthocarbonate was weighed and added dropwise to the reaction bottle. After the dropwise addition, the reaction solution was reacted at 10-30° C. for 15 hours. Add 50 mL of 15% ammonia water to the reaction solution at a temperature not higher than 20° C. and stir for ten minutes, then add 180 mL of purified water for washing and separation, and collect the organic layer. Concentrate the organic phase under reduced pressure at 40°C to obtain a colorless viscous liquid, add 80mL of petroleum ether, stir well, crystallize at low temperature (T<15°C) for more than 2h, and precipitate a white solid, w...
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