Ammonium Chloride → 1-Chloro-10,14-dimethylnonadeca-10,13-dien-7-yne

HRID 1606681Notes

Reaction equation

HRID 1606681 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[CH:9].C([Mg]Br)C.Br[CH2:15][C:16]([CH3:27])=[CH:17][CH2:18][CH:19]=[C:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[Cl-].[NH4+]>CCOCC.O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[C:9][CH2:15][C:16]([CH3:27])=[CH:17][CH2:18][CH:19]=[C:20]([CH3:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 903601-Octyne, 8-chloro-HCID 542631801-Bromo-2,6-dimethylundeca-2,5-dieneHCID 178418443HCID 178418443, compound

Product 1

HCID 536713201-Chloro-10,14-dimethylnonadeca-10,13-dien-7-yne

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 12.0 g. of 1-chlorooct-7-yne in 20 ml. of tetrahydrofuran is added to a mixture of 27 ml. of 3N ethyl magnesium bromide in ether and 50 ml. of tetrahydrofuran. The mixture is stirred and heated under reflux for 30 min. under nitrogen, then 0.45 g. of powdered cuprous chloride is added and heating and stirring is continued for 20 min. A solution of 20.0 g. of 1-bromo-2,6-dimethyl-2,5-undecadiene in 15-ml. of tetrahydrofuran is added and the mixture is heated under reflux for 10 hrs., then allowed to stand for about 18 hrs., and poured into saturated aqueous ammonium chloride and ether. The mixture is filtered and the ether solution is separated, washed with water, dried over sodium sulfate, and evaporated to leave a residue comprising 1-chloro-10,14-dimethylnonadeca-10,13-dien-7-yne.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 min. under nitrogen
  3. temperatureheating
  4. stirringstirring
  5. temperaturethe mixture is heated
  6. temperatureunder reflux for 10 hrs
  7. waitto stand for about 18 hrs
  8. filtrationThe mixture is filtered
  9. customthe ether solution is separated
  10. washwashed with water
  11. dry with materialdried over sodium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-0cca801f0c7d4f3499e42b514095badf
Source dataset
uspto-grants-1976_04
Patent number
US03953499

Reaction notes

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