Method for synthesizing p-methoxybenzaldehyde by taking anethole as raw material
A technology of p-methoxybenzaldehyde and anethole, which is applied in the field of flavors and fragrances, can solve the problems of high requirements for reaction conditions, difficult mass production, and low production efficiency, and achieve high selectivity, low production cost, and high production efficiency. Effect
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[0023] POL-PPh used in the present invention 3 The preparation method is as follows: dissolve 1.0g 3V-PPh3 in 10ml THF, then add 25mg azobisisobutyronitrile, mix well and transfer to the reaction kettle, react at 100°C for 24 hours, and evaporate the solvent in vacuo to obtain a white powdery POL- PPh3.
[0024] The 3V-PPh 3 The preparation process is as follows: 22 mmol of PPh 3 Dissolve in 30ml of THF, slowly drop it into the pre-prepared 4-vinylmagnesium bromide Grignard reagent at 0°C. After the dropwise addition, the reaction system was continued to react at room temperature for 2 hours, with saturated NH 4 The reaction was quenched with Cl solution, extracted with excess ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, and finally the product was purified with a silica gel column to obtain a white 3V-PPh3 solid.
Embodiment 1
[0026] A method for synthesizing p-methoxybenzaldehyde with anethole as a raw material, comprising the steps:
[0027] (1) Catalyst preparation: under argon atmosphere, 500 mg POL-PPh 3 , 25 mg PdCl 2 Put it into a 25 mL sealed tube, then add 5 mL of anhydrous THF, react at 30 °C overnight, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain 518 mg of yellow solid, which is POL-PPh 3 @PdCl 2 catalyst;
[0028] (2) Catalytic oxidation reaction: Weigh POL-PPh3@PdCl in a 250 mL round-bottomed flask 2 100 mg, then add anethole 1.482 g (10 mmol) and 40 mL of toluene, stir evenly, then add 16.1 g of 30% hydrogen peroxide aqueous solution (140 mmol hydrogen peroxide), and catalyze the oxidation reaction for 1 h under stirring at room temperature;
[0029] (3) Purification: The reaction solution obtained in step (2) was filtered through celite, left to stand for layers, the organic phase was washed twice with w...
Embodiment 2
[0032] A method for synthesizing p-methoxybenzaldehyde with anethole as a raw material, comprising the steps:
[0033] (1) Catalyst preparation: under argon atmosphere, 500 mg POL-PPh 3 , 40mg PdCl 2 Put it into a 25 mL sealed tube, then add 5 mL of anhydrous THF, react at 30°C overnight, filter, remove the filtrate, wash the filter residue twice with ethyl acetate and ethanol, and collect the solid to obtain POL-PPh 3 @PdCl 2 Catalyst 532 mg;
[0034] (2) Catalytic oxidation reaction: Weigh POL-PPh in a 250 mL round bottom flask 3 @PdCl 2 100 mg, then add 2.223 g (15 mmol) of anethole and 50 mL of toluene, stir well, then add 18.4 g of 30% aqueous hydrogen peroxide solution (160 mmol hydrogen peroxide), and catalyze the oxidation reaction under stirring at room temperature for 1.5 h;
[0035] (3) Purification: The reaction solution obtained in step (2) was filtered through quartz sand, left to stand for stratification, the organic phase was washed twice with water, and w...
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