Water → Ethyl 3-(4-fluorophenyl)acrylate

9.6 g. of sodium hydride (50% in mineral oil, pentane washed) is added in small portions to a solution of 45 g. of triethyl phosphonoacetate in 400 ml. of dry tetrahydrofuran stirred at 0° C. under nitrogen. The reaction mixture is allowed to warm to room temperature, stirred at room temperature for 1 hour and cooled to 10° C., a solution of 24.8 g. of 4-fluorobenzaldehyde in 25 ml. of dry tetrahydrofuran is adde dropwise, and the reaction mixture is stirred at room temperature for 18 hours, the reaction mixture being maintained under nitrogen throughout. Water is added to the reaction mixture. The reaction mixture is extracted twice with diethyl ether, and the organic layers are combined, dried over anhydrous sodium sulfate and evaporated at reduced pressure to an oil. The oil is distilled at 15 mm. Hg. to obtain the product (28.3 g. (73%)), b.p. 142° C.

1. temperaturecooled to 10° C.
2. stirringthe reaction mixture is stirred at room temperature for 18 hours
3. temperaturethe reaction mixture being maintained under nitrogen throughout
4. extractionThe reaction mixture is extracted twice with diethyl ether
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated at reduced pressure to an oil
7. distillationThe oil is distilled at 15 mm. Hg
8. customto obtain the product (28.3 g. (73%)), b.p. 142° C.

ORD record

ord-5865ea5e9c534ce39b35f187c3b4a17b

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04876280