Novel synthesis method of 4, 4, 4-trifluoro-1-butanol and homologue thereof
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A homologous, newly synthesized technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of low yield, high activity of tetrahydroaluminum lithium, and incompatibility.
Active Publication Date: 2021-05-11
万知科技股份有限公司
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The disadvantage of this method is that the activity of lithium aluminum hydride is high, and the post-treatment needs to add quenching reagents in strict proportion, which is not suitable for industrial scale-up.
The yield of this method is too low, and it does not have practical synthesis value. At the same time, this method uses Freon raw materials that will pollute the air, which is not suitable for modern environmental protection needs, and the reaction temperature is too high, which is likely to cause safety hazards
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Embodiment 1
[0033] (1) Preparation of formula (I) compound (2-benzyloxyethyl)-trifluoromethyl ketone
[0034]
[0035] Add 700mL of 2-benzyloxy-ethylmagnesium chloride (1M) dropwise to 1000mL of ethyl trifluoroacetate at -20°C, slowly return to room temperature, react for 6 hours, pour into 1000mL of water, adjust the pH to 5.0-6.8 with hydrochloric acid , collected the organic phase, and spin-dried the solvent to obtain (2-benzyloxyethyl)-trifluoromethyl ketone. The crude product was temporarily overweight and was directly used in the next reaction.
[0036] (2) Preparation of formula (II) compound 1-benzyloxy-4,4,4-trifluorobutane
[0037]
[0038] Dissolve (2-benzyloxyethyl)-trifluoromethyl ketone obtained in the previous step in 900mL DMSO, add 50g hydrazine hydrate, react at room temperature for 2 hours, slowly add 200g potassium tert-butoxide in batches, continue to Reacted at room temperature for 12 hours, poured into ice water, adjusted to neutral with hydrochloric acid, ex...
Embodiment 2
[0043] The preparation process is substantially the same as in Example 1, except that:
[0044] In step (3), the organic solvent is 1,2-dichloroethane, the Lewis acid is aluminum trichloride, and the three-step total reaction yield is 75%.
Embodiment 3
[0046] The preparation process is substantially the same as in Example 1, except that:
[0047] In step (3), the organic solvent is chloroform, the Lewis acid is hydrobromic acid, and the three-step total reaction yield is 69%.
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Abstract
The invention discloses a novel synthesis method of 4, 4, 4-trifluoro-1-butanol and a homologue thereof, and relates to the technical field of organic synthesis. The method mainly comprises the following steps of: (1) reacting ethyl trifluoroacetate with a Grignard reagent to prepare benzyloxy substituted alkyl-trifluoromethyl ketone; (2) carrying out reduction reaction on the benzyloxy substituted alkyl-trifluoromethyl ketone to prepare 1-benzyloxy-trifluorosubstituted alkyl; and (3) carrying out hydrolysis on the 1-benzyloxy-trifluorosubstituted alkyl, so as to prepare 4, 4, 4-trifluoro-1-butanol or a homologue thereof disclosed by the invention. Compared with the prior art, Freon raw materials which can pollute air are not used; dangerous lithium aluminum hydride is not used; high-temperature reaction is not needed; and the raw material ethyl trifluoroacetate is cheap and easily available, and the other main raw material Grignard reagent can also be synthesized from cheap raw materials.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a new synthesis method of 4,4,4-trifluoro-1-butanol and its homologues. Background technique [0002] 4,4,4-Trifluoro-1-butanol, formula C 4 h 7 f 3 O, the relative molecular mass is 128.09, the appearance is a colorless transparent liquid, and its structural formula is as follows: [0003] [0004] Due to the high electronegativity of fluorine atoms, 4,4,4-trifluoro-1-butanol has a strong ability to form hydrogen bonds, and other chemical substances will generate more stable compounds; compared with compounds without fluorine, This kind of fluorine-containing compounds has the characteristics of less dosage, low toxicity, high efficacy, and strong metabolism in the properties of medicines and pesticides. They are widely used as drugs with stronger biological activity and higher selectivity. 4,4,4-Trifluoro-1-butanol can be used in medicine to prepare lactones an...
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