Formaldehyde → HCID 14652260, compound

Temperature

95 °C

A mixture of paraformaldehyde (21.42 g, 714 mmol), diethylamine (82.2 mL, 801 mmol) and copper(11) acetate (2 g) was heated at 60° C. in dioxane (120 mL). After 1.4 hours pent-4-yn-1-ol (60 g, 714 mmol) was added and the mixture was heated at 95° C. for 3 hours. The cooled reaction mixture was poured onto 10% potassium hydroxide (120 mL) and the resulting mixture was filtered through Celite which was washed with diethyl ether. The organic layer was separated and washed with water (3×120 mL). The aqueous extract was back-extracted with methylene chloride (3×100 mL). The combined organic layers were washed with brine, dried (MgSO4), and evaporated at reduced pressure. The residue was Kugelrohr distilled to afford 102 g (99%) of the product as an oil. 1H NMR (CDCl3)δ: 1.13 (t, 6H), 1.72 (quintet, 2H), 2.31 (t, 2H), 2.55 (q, 4H), 3.38 (d, 2H), 3.68 (t, 2H), 3.95 (s, 1H) ppm.

1. customThe cooled reaction mixture
2. filtrationthe resulting mixture was filtered through Celite which
3. washwas washed with diethyl ether
4. customThe organic layer was separated
5. washwashed with water (3×120 mL)
6. extractionThe aqueous extract
7. extractionwas back-extracted with methylene chloride (3×100 mL)
8. washThe combined organic layers were washed with brine
9. dry with materialdried (MgSO4)
10. customevaporated at reduced pressure
11. distillationdistilled

ORD record

ord-c655ec089ea44c259aeca81e9a6f5ee5

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877779