Hydrochloric Acid → Ethyl (chloroformyl)acetate

To a three neck 2 L round bottom flask charged with potassium t-butoxide (0.5 mol. 500 mL of a 1M solution in THF) and 500 mL of dry THF cooled to 0° C. was added dropwise from an addition funnel a solution of ethyl chloroacetate (0.5 mol, 53.5 mL) and ethyl formate (0.5 mol, 40.4 mL), in 200 mL of THF over 3 hours. After completion of addition, the reaction mixture was stirred for 1 hour and allowed to stand overnight. The resulting solid was diluted with diethyl ether and cooled in an ice bath. Then, the pH was lowered to approximately 3 using 6N HCl. The organic phase was separated, and the aqueous layer was washed 3 times with diethyl ether. The combined ethereal portions were dried over NaSO4, and concentrated in vacuo. The crude desired compound was stored at −30° C. and used without further purification.

1. additionAfter completion of addition
2. waitto stand overnight
3. temperaturecooled in an ice bath
4. customThe organic phase was separated
5. washthe aqueous layer was washed 3 times with diethyl ether
6. dry with materialThe combined ethereal portions were dried over NaSO4
7. concentrationconcentrated in vacuo
8. customwas stored at −30° C.
9. customused without further purification

ORD record

ord-74df098d38514209aea3dc412c5dd612

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313296B1