3-Ethoxyacryloyl chloride

light yellow liquid

Used as an intermediate in organic synthesis.

Journal of Heterocyclic Chemistry, 13, p. 1015, 1976 DOI: 10.1002/jhet.5570130515
Synthesis, p. 1079, 1993

To a solution of ethyl 3,3-diethoxypropionate (20 g) in water (50 mL) was added sodium hydroxide (5 g) at room temperature and the reaction was heated to 110°C and stirred at this temperature for 1 hour. Then the reaction system was naturally cooled to room temperature, diluted with water (2L), extracted with ethyl acetate (1L), the extract was washed with saturated brine (1L), dried over anhydrous sodium sulfate and filtered; the filtrate was directly concentrated to obtain To the crude was added thionyl chloride (30 mL) and the reaction was heated to 70°C and stirring was continued at this temperature for one hour. After the reaction, the reaction solution was directly concentrated under reduced pressure to obtain a brown solid 3-Ethoxyacryloyl chloride (14 g, yield 90%).

[1] Patent: WO2009/140342, 2009, A1. Location in patent: Page/Page column 118-119
[2] Patent: US2014/142114, 2014, A1. Location in patent: Paragraph 0464; 0465