Acetic Acid → 2-Methyleneheptan-1-al

Temperature

50 °C

A 3-liter three-neck flask fitted with an overhead stirrer and condenser was charged with di-N-butyl amine (33 g, 0.25 mol) and acetic acid (31 g, 0.5 mol). Roughly 500 ml of 33% formaldehyde solution in water (178 g formaldehyde, 5.9 mol) was then added and the resulting solution was heated to 50° C. with stirring. After this temperature was reached heptanal (500 g, 4.3 mol) was fed in over about 1.5 h. A slight exotherm was noticed during the feed. Monitoring by GC showed the consumption of heptanal and the production of 2-methylene heptanal, 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 carbonate, then taken directly on to the next step.

1. customA 3-liter three-neck flask fitted with an overhead stirrer and condenser
2. customwas fed in over about 1.5 h
3. customthe consumption of heptanal
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 carbonate

ORD record

ord-3e727f49a764460db94b13772b122eaa

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678749B2