Long-chain alkanoic acid derivative as well as preparation method and application thereof
A technology of long-chain alkanoic acid and long-chain hydroxyalkanoic acid, applied in organic chemistry, etc., can solve the problems of lack of reports, lack of long-chain alkyldiacid mono-tert-butyl ester, lack of research on long-chain alkanoic acid derivatives, etc. Achieve high production efficiency, mild conditions and simple reaction process
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[0040] A preparation method of long-chain alkanoic acid derivatives, comprising the following steps:
[0041] The long-chain hydroxyalkanoic acid derivative shown in E is reacted in the presence of sodium borohydride to prepare the long-chain alkanoic acid derivative shown in D. In the following equation, n is an integer greater than or equal to 0;
[0042]
[0043] As preferably, the specific steps of generating D by E reaction are as follows:
[0044] Add dichloromethane to E to dissolve, lower the temperature to -5°C to 5°C, add acetic acid to stir, add sodium borohydride to react for 1 to 2 hours, extract twice with saturated sodium bicarbonate solution, first wash with purified water, and then use Wash with saturated brine, dry over anhydrous sodium sulfate, and beat with methyl tert-butyl ether as a solvent to obtain D.
[0045] Preferably, in the specific step of preparing D from E, the molar ratio of E to acetic acid is 1:8-15, and optimally, the molar ratio of E t...
Embodiment 1
[0060] Preparation of tetradecanoic acid derivatives with tetradecanedioic acid as raw material:
[0061] (1) Condensation of tetradecanedioic acid and isopropylidene malonate to prepare 14-(2,2-dimethyl-4,6-dioxy-1,3-dioxanyl-5-ene base)-14-hydroxytetradecanoic acid
[0062]
[0063] Concrete reaction process is as follows:
[0064] Under the protection of nitrogen, add 20g (77mmol) of tetradecanedioic acid, 11.1g (77mmol) of isopropylidene malonate and dichloromethane (400ml) into the reaction flask respectively, stir, and cool down to -2°C~- 6°C, add 9.4g (77mmol) of 4-dimethylaminopyridine, react for 8-12min, then add 9.7g (77mmol) of N,N'-diisopropylcarbodiimide, move to room temperature and react for 12h, then Treatment was extracted twice with 10% aqueous citric acid (200ml), washed once with purified (200ml) water, washed with saturated brine (200ml), and the organic phase was dried with anhydrous sodium sulfate (20g); the solvent was removed by rotary evaporation...
Embodiment 2
[0076] Preparation of tetradecanoic acid derivatives with tetradecanedioic acid as raw material:
[0077] (1) Condensation of tetradecanedioic acid and isopropylidene malonate to prepare 14-(2,2-dimethyl-4,6-dioxy-1,3-dioxanyl-5-ene base)-14-hydroxytetradecanoic acid
[0078]
[0079] Concrete reaction process is as follows:
[0080] Under the protection of nitrogen, add 20g (77mmol) of tetradecanedioic acid, 12.2g (84.7mmol) of isopropylidene malonate and dichloromethane (400ml) respectively in the reaction flask, stir, and cool down to -2°C~ -6°C, add 14g (115.5mmol) of 4-dimethylaminopyridine, react for 8-12min, then add 10.7g (84.7mmol) of N,N'-diisopropylcarbodiimide, move to room temperature for 12h , the post-treatment was extracted twice with 10% aqueous citric acid (200ml), washed once with purified water (200ml), washed with saturated brine (200ml), and the organic phase was dried with anhydrous sodium sulfate (20g); the solvent was removed by rotary evaporation...
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