Overview[1]
Ethyl 3-benzoyl acrylate can be used as a pharmaceutical synthesis intermediate. To date, the most common method for synthesizing esters is through a dehydration reaction between a carboxylic acid and an alcohol, which has been used to synthesize O-benzoyl acrylates, such as ethyl 3-benzoyl acrylate. In the case of a dehydration reaction between β-benzoyl acrylic acid and ethanol, ethyl 3-benzoyl acrylate has been reported to be obtained in good yields.
Preparation[1-2]
The preparation method of 3-benzoyl ethyl acrylate is as follows:
Method 1: 3-Benzoylacrylic acid ethyl ester is prepared as follows: stir a mixture of 2.0 g of ethyl glyoxylate acetal, 1.37 g of acetophenone, 0.02 g of sulfuric acid and 20 ml of toluene at 110 The reaction was carried out for 12 hours at ℃, and the mixed solvent of water, ethanol and toluene produced during the reaction was distilled off until the total volume of the reaction mixture became half. After cooling the reaction mixture by standing, the reaction mixture was partitioned between the toluene-water phase. The toluene phase was washed with saturated aqueous sodium bicarbonate solution, then with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 3.25 g of yellow oil, which contained 2.54 g of 3-benzoyl ethyl acrylate.
Method 2: Stir a mixture of 6.45g ethyl trans-B-benzoyl ethyl acrylate, 3.55g β-benzoyl-α-ethoxypropionic acid ethyl ester and 1.80g sulfuric acid at 100°C. At the same time, use an aspirator to reduce the pressure to 20mmHg and distill it off. Produce ethanol. The reaction was continued for 10 minutes and then cooled to obtain 7.763-ethyl benzoyl acrylate.
Main reference materials
[1] EP0494620 Process for preparing trans-beta-aroylacrylic ester.
[2] EP0204286 Process for preparing trans-beta-benzoylacrylic acid ester.
