Water → HCID 14478659, compound

A solution of 142.23 g (1.02 mol) of N-[1-(E)-penten-1-yl]pyrrolidine and 100 mL (80.6 g, 1.52 mol) of acrylonitrile in 570 mL of 1,4-dioxane was heated at gentle reflux, under argon, for 16 hr. 50 mL of water was then added and the mixture was stirred at reflux for a further 8 hr. After concentration in vacuo, 200 g of ice, 400 mL of 3N hydrogen chloride solution, and 600 mL of methylene chloride were added, and the mixture was stirred for 15 min. The aqueous layer was separated and extracted with 3×300 mL of methylene chloride, and the combined organic layers were washed with 2×150 mL of saturated brine, dried (MgSO4), filtered and concentrated. The residue (140.2 g) was distilled to give 46.96 g (33.0%) of 4-formylheptanenitrile bp 103°-104° C. (1.33 mm Hg).

1. temperatureat reflux for a further 8 hr
2. concentrationAfter concentration in vacuo, 200 g of ice, 400 mL of 3N hydrogen chloride solution, and 600 mL of methylene chloride
3. additionwere added
4. stirringthe mixture was stirred for 15 min
5. customThe aqueous layer was separated
6. extractionextracted with 3×300 mL of methylene chloride
7. washthe combined organic layers were washed with 2×150 mL of saturated brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. distillationThe residue (140.2 g) was distilled

ORD record

ord-eb68a23a3eab4e9e83fd1d80a99eabeb

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897477