Diethylene Glycol → HCID 20264430, compound

Temperature

180 °C

A mixture of 4-n-butoxy-1-n-propylbicyclo(2,2,2)octane-2-one (2.08 g, 0.009 mol) hydrazine hydrate (8.4 ml, 98-100%) and potassium hydroxide (2.80 g, 0.050 mol) in diethylene glycol (40 mol) was stirred and heated under reflux for 4 h (180° C., oil bath temperature). The reaction mixture was cooled and hydrazine hydrate (4 ml) and potassium hydroxide (1.00 g) were added and the apparatus was arranged for distillation. The temperature was raised slowly to 240° C. in 2 h, and the reaction mixture was kept at this temperature for 2 h. The reaction mixture was cooled and the residue and the distillate were separately diluted with water, washed with ether (3×50 ml). All the ether washings were combined and washed with water (2×50 ml) dilute hydrochloric acid (2×50 ml) and water (2×50 ml). The ether solution was dried (MgSO4) and ether was removed to give a residue which was chromatographed on a neutral alumina column (1.5×30 cm) using light petroleum (bp 40°-60° C.) as eluent. Four fractions were collected (20 ml each) the solvent was removed to leave a residue which was distilled in a short-path distillation apparatus under reduced pressure to give the required compound.

1. temperatureheated
2. temperatureThe reaction mixture was cooled
3. distillationthe apparatus was arranged for distillation
4. temperatureThe temperature was raised slowly to 240° C. in 2 h
5. temperatureThe reaction mixture was cooled
6. additionthe residue and the distillate were separately diluted with water
7. washwashed with ether (3×50 ml)
8. washwashed with water (2×50 ml) dilute hydrochloric acid (2×50 ml) and water (2×50 ml)
9. dry with materialThe ether solution was dried (MgSO4) and ether
10. customwas removed
11. customto give a residue which
12. customwas chromatographed on a neutral alumina column (1.5×30 cm)
13. customFour fractions were collected (20 ml each) the solvent
14. customwas removed
15. customto leave a residue which
16. distillationwas distilled in a short-path distillation apparatus under reduced pressure

ORD record

ord-fdc98bfba8d44447a834e0731edcbc28

Source dataset

uspto-grants-1985_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04544497