A kind of preparation method of 3-oxo-2-pentyl-cyclopentenyl acetate
A technology of methyl cyclopentenyl acetate and methyl dihydrojasmonate is applied in the preparation of carboxylate, the preparation of organic compounds, the separation/purification of carboxylate, etc. Inappropriate, complex process and other problems, to achieve the effect of reuse, high safety and simple operation
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[0044] A kind of preparation method of DHH comprises the following steps: (1) as can be seen in the above-mentioned reaction, first commercially available common methyl dihydrojasmonate is dissolved in solvent, then add DDQ reaction to obtain end product crude product and The by-product DDHQ, this synthetic preparation route is obtained from the commercially available common methyl dihydrojasmonate, which is dehydrogenated in one step under the action of DDQ. Only one-step reaction reduces the time cost of production, and the reaction is fast, the operation is simple, the yield is high, and the industrial scale-up production is easy. This synthetic preparation route is based on the amount of methyl dihydrojasmonate, the amount of DDQ is 1-1.5 times the number of moles of methyl dihydrojasmonate, and the optimal amount is 1.2 times; The amount of the solvent is 8-12 times, preferably 10 times, the number of moles of the methyl dihydrojasmonate, and the solvent is selected from ...
Embodiment 1
[0048] Add 150mL 1,4-dioxane, 15g (0.066mol) of commercially available methyl dihydrojasmonate into a 500mL three-necked flask, stir and dissolve, add DDQ 18.1g (0.08mol), and heat up to reflux (temperature is 101 ℃) for 12 hours. After cooling down to room temperature, the solid was removed by filtration (the main components were unreacted DDQ and DDHQ produced by reduction of DDQ), and the filter cake was washed once with 20 mL of 1,4-dioxane. After removing the solvent 1,4-dioxane, 150 mL of water was added to the concentrate, and then 100 mL of ethyl acetate was added for extraction once. The ethyl acetate layer was washed twice with 5% aqueous sodium chloride solution, 50 mL each time. After the ethyl acetate layer was concentrated, 15.8 grams of the crude product of the final product were obtained, and after purification by a silica gel column, 10.2 grams of the final product DHH were obtained, and the final product was a colorless oil, such as figure 1 Shown, the puri...
Embodiment 2
[0050] Based on Example 1, the only difference between Example 2 and Example 1 is: add 150mL 1,4-dioxane, 15g (0.066mol) of commercially available methyl dihydrojasmonate to a 500mL three-necked flask, After stirring and dissolving, 15.0 g (0.066 mol) of DDQ was added, and 0.74 g (0.007 mol) of commercially available 85% phosphoric acid was added. The temperature was raised to reflux (the temperature was 101° C.) and the reaction was carried out for 8 hours. 7.8 g of the final product DHH was obtained, the purity of which was checked by gas chromatography was 96.3%, the reaction yield was 52.3%, and the structure was confirmed to be correct by nuclear magnetic characterization.
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