Method for synthesizing (cis)-(6-methoxyl-1-carbonyl-3,4 dihydronaphthyl-2(1H)-ylidene) methyl benzoate
A technology of methyl benzoate and dihydronaphthyl, applied in the field of organic synthesis, can solve the problems of bad smell, difficult recovery, low product yield, etc., to avoid the formation of impurities and trans isomers, and reduce stimulation Odor, the effect of high product purity
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Embodiment 1
[0047] Equipped with mechanical stirring, thermometer, N 2 Add 5.51g of sodium methoxide to a protected dry 250mL four-neck flask, then add 35mL of toluene at a temperature of 16°C, then dropwise add 7.57g (about 0.1mol) of ethyl formate, and dropwise add 35mL of 6 -Toluene solution of methoxy-1-tetralone (including 6.00 g of 6-methoxy-1-tetralone, 0.034 mol), the temperature of the dropwise addition is 20°C, the reaction is stirred at room temperature for 1 h, and the 6-methanone is detected by HPLC. The content of oxy-1-tetralone is 0.799% (less than 1.0%). Cool in an ice bath to 0°C, add 102mL of aqueous hydrochloric acid solution with a concentration of 1mol / L, separate the liquids, wash the organic phase with 2×50mL water, and add 20mL of the organic phase Toluene, 20 mL was rotovapped off. Add the remaining liquid into a 500mL four-necked flask equipped with a mechanical stirrer and a thermometer, add 90mL of toluene, add 3.44g of triethylamine, cool in an ice bath to 0...
Embodiment 2
[0049] Equipped with mechanical stirring, thermometer, N 2Add 4.76g of potassium methoxide to a protected dry 250mL four-neck flask, then add 35mL of dichloromethane at a temperature of 16°C, then add 5.04g of ethyl formate (about 0.0681mol) dropwise, and add dropwise at a temperature of 18°C, then add dropwise 35mL dichloromethane solution of 6-methoxy-1-tetralone (including 6.00g, 0.034mol of 6-methoxy-1-tetralone), the temperature of the completion of the addition is 20°C, the reaction is stirred at room temperature for 2h, HPLC Detect 6-methoxyl-1-tetralone content 0.308% (less than 1.0%) in an ice bath and cool to 0°C, add 34mL of 1mol / L sulfuric acid aqueous solution, separate the layers, and extract the aqueous layer with 4×10mL dichloromethane, The organic layers were combined and 37 mL was rotovapped off. Add the remaining liquid to a 500mL four-necked flask equipped with mechanical stirring and a thermometer, add 3.44g triethylamine, dropwise add 4.78g benzoyl chlor...
Embodiment 3
[0051] Equipped with mechanical stirring, thermometer, N 2 Add 4.62g of sodium ethoxide to a protected dry 250mL four-neck flask, then add 35mL of ethyl acetate, then dropwise add 5.04g of ethyl formate (about 0.0681mol), and dropwise add 35mL of 6-methanol Oxy-1-tetralone ethyl acetate solution (including 6-methoxy-1-tetralone 6.00g, 0.034mol), the temperature of the completion of the dropwise addition was 19°C, and the reaction was stirred at room temperature for 2h. The content of oxy-1-tetralone is 0.109% (less than 1.0%), add 68mL of 1mol / L phosphoric acid, separate the layers, extract the aqueous layer with 3×10mL ethyl acetate, combine the organic layers, and rotary evaporate 20mL of ethyl acetate . Add the remaining liquid into a 500mL four-neck flask equipped with a mechanical stirrer and a thermometer, add 4.12g of dimethylaniline, cool in an ice bath to 2°C, add 4.78g of benzoyl chloride (0.034mol) dropwise, and then add 20mL of ethyl acetate The ester was dissolv...
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