Preparation and application of 4-propoxybenzaldehyde_Kain Industrial Additive

Background and overview^[1]

4-Propoxybenzaldehyde, also called p-propoxybenzaldehyde, can be prepared by the one-step reaction of p-hydroxybenzaldehyde and n-bromopropane.

Preparation^[1]

Add 30ml DMF to p-hydroxybenzaldehyde (12.2g, 100mmol, 1eq), n-bromopropane (0.8-1.5eq) and potassium carbonate (1~3eq), stir at 50~100℃ for 5~16 hours, and perform TLC ( PE:EA=5:1) shows that a new point with less polarity is generated, and there is still a small amount of p-hydroxybenzaldehyde that has not reacted completely. Cool to room temperature, add 100ml dichloromethane and 100ml water to the reaction solution, extract and separate layers, wash the organic phase twice with water, add about 20g anhydrous sodium sulfate to the organic phase, dry for about 30 minutes, filter out the inorganic The salt and organic phase were separated using a 200-300 mesh silica gel column (eluent was gradient elution from petroleum ether to petroleum ether: ethyl acetate = 5:1) to obtain pure 4-propoxybenzaldehyde.

Apply^[1]

CN201410043200.5 reported that 4-propoxybenzaldehyde can be used to prepare 1,3-bis(p-propoxydibenzylamine)guanidine hydrochloride. This compound is a diaminoguanidine derivative that promotes animal growth. Through feeding experiments, this patent found for the first time that the production performance of ducks was significantly improved after applying this diaminoguanidine compound. This study also found through animal feeding experiments that the production performance of pigs and chickens was improved after applying such diaminoguanidine compounds. The preparation method is as follows: Dissolve 4-propoxybenzaldehyde (12.4g, 0.09mol, 2eq) in about 150ml of ethanol, then add diaminoguanidine monohydrochloride ((0.7~1.5eq)), 10~70 Stir for 17 hours at ℃, diaminoguanidine monohydrochloride gradually dissolves, and a large amount of white solid precipitates. Filter, wash the filter cake with ethanol (50ml*2), and spin the solid to dryness with a water bath at 40℃ to obtain the product.

Main reference materials

[1][China invention, China invention authorization] CN201410043200.5 diaminoguanidine derivative and its application in the preparation of animal feed growth promoter