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 ethyl formate (17.2 mL, 213 mmol) and ethyl chloroacetate (22.79 mL, 213 mmol) as a solution 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 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give 1B (4.5 g, 15.4% 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 times)
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated

ORD record

ord-060ba42a549f40b8b5a70bb1f396fc9d

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252795B2