Sodium Iodide → Iodomethyl 2-ethylbutanoate

2-Ethyl butyric acid chloromethyl ester (700 g) was dissolved in acetone (3 L). To this solution was added sodium iodide (1.0 kg). The resulting reaction mixture was heated at reflux until reaction completion (2 h (hours), monitored by GC). The solution was then cooled to ambient temperature where tert-butyl methyl ether (7 L) and 5% aqueous sodium thiosulfate (4 L) were added. The phases were separated and the organic phase was washed with aqueous sodium thiosulfate (4 L), low pyrogen water (4 L) and 10% sodium chloride solution (4 L). The organic layer was dried over magnesium sulfate (350 g), filtered, and the filter cake was washed with tert-butyl methyl ether (2×0.7 L). The filtrate was evaporated to a small volume (ca. 2 L) to give 2-ethyl butyric acid iodomethyl ester, as a solution in tert-butyl methyl ether.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureat reflux until reaction completion (2 h (hours), monitored by GC)
4. additionwere added
5. customThe phases were separated
6. washthe organic phase was washed with aqueous sodium thiosulfate (4 L), low pyrogen water (4 L) and 10% sodium chloride solution (4 L)
7. dry with materialThe organic layer was dried over magnesium sulfate (350 g)
8. filtrationfiltered
9. washthe filter cake was washed with tert-butyl methyl ether (2×0.7 L)
10. customThe filtrate was evaporated to a small volume (ca. 2 L)

ORD record

ord-6a87a732bff64763affb64fc22f717d1

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07795244B2