Acetylene → 1,1-Dimethoxy-oct-7-yne

Acetylene was bubbled through ca. 300 ml of liquid ammonia while 8.1 g (0.35 atom) of sodium was added in small pieces. After the disappearance of the blue color, dimethylsulfoxide (150 ml) was added cautiously. 1,1-Dimethoxy-6-iodohexane (8.16 g; 0.3 Mole) was then added over a period of 10 min. while acetylene was bubbled through the stirred mixture. The ammonia was allowed to evaporate and was replaced with ether. When the mixture had reached 0°, dilute NH4Cl solution was added. The organic layer was separated, washed with water, dried (Na2SO4), and evaporated. Distillation of the residue gave 48.9 g (96%) of 1,1-dimethoxy-oct-7-yne, b.p. 91°/8 Torr.

1. customAcetylene was bubbled through ca. 300 ml of liquid ammonia while 8.1 g (0.35 atom) of sodium
2. additionwas added in small pieces
3. additionAfter the disappearance of the blue color, dimethylsulfoxide (150 ml) was added cautiously
4. customwas bubbled through the stirred mixture
5. customto evaporate
6. customhad reached 0°
7. additiondilute NH4Cl solution was added
8. customThe organic layer was separated
9. washwashed with water
10. dry with materialdried (Na2SO4)
11. customevaporated
12. distillationDistillation of the residue

ORD record

ord-4565cebe301f4b799e3edc3771241e31

Source dataset

uspto-grants-1982_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04346023