Ethanol → Ethyl (chloroformyl)acetate

To a flask was added sodium (4.45 g, 194 mmol) and ethanol (56.5 mL, 968 mmol) and the mixture was stirred at room temperature for 4 hours until all of the metal had dissolved. Diethyl ether (100 mL) was added, followed by the slow addition of a solution of ethyl formate (17.20 mL, 213 mmol) and ethyl chloroacetate (22.79 mL, 213 mmol) in diethyl ether (100 mL). The reaction solution was stirred at room temperature for 16 hours. The resulting precipitate that formed was filtered and washed with ether, and dissolved in water. The aqueous layer was acidified with HCl (1N) to pH 4 and the product was extracted with diethyl ether (3×). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give ethyl 2-chloro-3-oxopropanoate (4.5 g, 29.9 mmol, 15.44% yield).

1. dissolutionhad dissolved
2. stirringThe reaction solution was stirred at room temperature for 16 hours
3. customThe resulting precipitate that formed
4. filtrationwas filtered
5. washwashed with ether
6. dissolutiondissolved in water
7. extractionthe product was extracted with diethyl ether (3×)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated

ORD record

ord-52b14f5d6798460aad80e938f7435b5c

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389527B2