Acetic Acid → 2-Methylene-octanal

Temperature

50 °C

A 5-liter flask fitted with an overhead stirrer and condenser was charged with di-N-butyl amine (61 g, 0.47 mol) and acetic acid (56 g, 0.9 mol). Roughly 900 ml of 37% formaldehyde solution in water (351 g formaldehyde, 11.7 mol) was then added and the resulting solution was heated to 50° C. with stirring. After this temperature was reached octanal (1000 g, 7.0 mol) was fed in over about 2 h. A slight exotherm was noticed during the feed. Monitoring by GC showed the consumption of octanal and the production of 2-methylene octanal, finally reaching roughly 95% conversion after the addition was complete. The reaction mixture was allowed to cool to room temperature, poured into a separatory funnel, and washed once with 5% HCl solution. The organic layer was then washed once with saturated sodium bicarbonate, then taken directly on to the next step.

1. customA 5-liter flask fitted with an overhead stirrer and condenser
2. customwas fed in over about 2 h
3. customthe consumption of octanal
4. additionafter the addition
5. temperatureto cool to room temperature
6. additionpoured into a separatory funnel
7. washwashed once with 5% HCl solution
8. washThe organic layer was then washed once with saturated sodium bicarbonate

ORD record

ord-5716b618c32145f9a2b7e53108cf8036

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678749B2