Diethyl Ether → 99028-44-1

A slurry of 50.0 gm (405 mmol) of ethyl acetimidate hydrochloride in 500 ml of methylene chloride was mechanically stirred and treated dropwise with 81.9 gm (809 mmol) of triethylamine while keeping the temperature at less than 25° C. The resulting slurry was then treated dropwise with 31.8 gm (405 mmol) of acetyl chloride while keeping the temperature at less than 30° C. The white slurry was stirred for one hour at room temperature, after which the methylene chloride was removed in vacuo. The white, oily mass obtained was then stirred with 400 ml of ether and filtered. The white solid obtained was washed with additional ether and the combined filtrate was concentrated in vacuo to afford 48.6 gm (93 percent) of a pale, yellow oil. IR and NMR spectra were consistent with the assigned structure.

1. customat less than 25° C
2. customat less than 30° C
3. customafter which the methylene chloride was removed in vacuo
4. customThe white, oily mass obtained
5. filtrationfiltered
6. customThe white solid obtained
7. washwas washed with additional ether
8. concentrationthe combined filtrate was concentrated in vacuo
9. customto afford 48.6 gm (93 percent) of a pale, yellow oil

ORD record

ord-a3f93e06bdb3443090fa16797409ab1b

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04685958