Acetylene → 1,1-Dimethoxy-oct-7-yne

HRID 1155594

Reaktionsgleichung

Reaktionsgleichung von HRID 1155594
[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]I.[CH:12]#[CH:13]>>[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:12]#[CH:13]

Komponenten

3

Edukt 2

HCID 6326AcetyleneHCID 205268401,1-Dimethoxy-6-iodohexane

Produkt 1

HCID 205268491,1-Dimethoxy-oct-7-yneAusbeute 96 %

Versuchsvorschrift

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 (81.6 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1bea7fb7f79a40a89d0046efcf100c59
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04302607

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