Acetic Acid → HCID 86762526, compound

Temperature

-10 °C

A reaction flask was charged with sec-butylmagnesium chloride (2 M, 1.6 L) and cooled to −10° C. 3-Methyl-butyraldehyde (260 g) was fed over about 2 hours while the temperature was kept under 15° C. The reaction mixture was aged to room temperature over about 6 hours and then poured into a mixture of ice and acetic acid (216 g). Toluene (400 mL) was added and aqueous and organic layers were split. The organic layer was separated and washed sequentially with sodium carbonate, brine, and water. The resulting organic layer containing crude 2,5-dimethyl-heptan-4-ol, crotonic acid (129 g), toluene (150 mL), and PTSA (10 g) were then charged into to 3-L reaction flask fitted with a Bidwell-Sterling trap. The reaction mixture was heated to reflux. Water was collected and removed via the Bidwell-Sterling trap. The reaction mixture was aged at reflux for about 18-20 hours till GC analysis showed completion of the reaction. The resulting reaction mixture was washed sequentially with sodium carbonate (twice) and brine, rush-over distilled and further fractional distilled to provide but-2-enoic acid 1-isobutyl-2-methyl-butyl ester (143 g) with a boiling point of 100° C. at 0.72 mmHg.

1. customwas kept under 15° C
2. customaqueous and organic layers were split
3. customThe organic layer was separated
4. washwashed sequentially with sodium carbonate, brine, and water
5. additionThe resulting organic layer containing crude 2,5-dimethyl-heptan-4-ol, crotonic acid (129 g), toluene (150 mL), and PTSA (10 g)
6. additionwere then charged into to 3-L reaction flask
7. customfitted with a Bidwell-Sterling trap
8. temperatureThe reaction mixture was heated to reflux
9. customWater was collected
10. customremoved via the Bidwell-Sterling trap
11. temperatureat reflux for about 18-20 hours till GC analysis
12. customcompletion of the reaction
13. customThe resulting reaction mixture
14. washwas washed sequentially with sodium carbonate (twice) and brine
15. distillationrush-over distilled
16. distillationfurther fractional distilled

ORD record

ord-d89eaddee33b479b9435b8b23762c0f0

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772533B1