Ethanol → Ethyl (chloroformyl)acetate

139 ml of a 21% strength solution of sodium ethoxide in ethanol (371 mmol, 0.91 equivalent) were initially charged in 200 ml of diethyl ether, and a solution of 43.7 ml of ethyl chloroacetate (408 mmol, 1 equivalent) and 32.9 ml of ethyl formate (408 mmol, 1 equivalent) in 150 ml of diethyl ether was added dropwise at RT. The reaction mixture was stirred overnight and the solid was filtered off and washed with diethyl ether. The solid was dissolved in water and the aqueous phase was, with ice bath cooling, adjusted to pH4 using concentrated hydrochloric acid. The mixture was extracted repeatedly with diethyl ether and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried with magnesium sulphate, filtered and concentrated. The crude product obtained (8.2 g) was freed from residual solvent under high vacuum and used without further purification for the next reaction.

1. filtrationthe solid was filtered off
2. washwashed with diethyl ether
3. dissolutionThe solid was dissolved in water
4. customthe aqueous phase was, with ice bath
5. temperaturecooling
6. extractionThe mixture was extracted repeatedly with diethyl ether
7. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
8. dry with materialdried with magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-780105da14fb4bfa9f54c0bd2fa589d9

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126998B2