Sodium Hydroxide → 1,6-Dichloro-3,3,6-trimethylhept-1-yne

HRID 1195020Notes

Reaction equation

HRID 1195020 reaction equation
[Cl:1][C:2](Cl)(Cl)[CH2:3][C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][C:7]([Cl:10])([CH3:9])[CH3:8].[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl>[Cl:1][C:2]#[C:3][C:4]([CH3:12])([CH3:11])[CH2:5][CH2:6][C:7]([Cl:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15919150HCID 15919150, compound

Product 1

HCID 159191511,6-Dichloro-3,3,6-trimethylhept-1-yneYield 78.9%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

25.2 g of 1,1,1,6-tetrachloro-3,3,6-trimethylheptane is heated with 0.60 g of tricaprylmethylammonium chloride ("Aliquat" 336) and 50 ml of 40% aqueous sodium hydroxide solution under vigorous agitation to 80° C. for 22 hours. The mixture is then allowed to cool, combined with 60 ml of dichloromethane, the organic phase is separated and dried over calcium chloride. The solvent is thereafter removed under vacuum, and the residue is distilled, thus obtaining 14.7 g of 1,6-dichloro-3,3,6-trimethyl-1-heptyne as a yellow oil, bp 39°-43° C. under 1 mbar.

Workup

  1. temperatureto cool
  2. customthe organic phase is separated
  3. dry with materialdried over calcium chloride
  4. customThe solvent is thereafter removed under vacuum
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-a875c0fd9bba4c40badfe7d0bf67f1a9
Source dataset
uspto-grants-1989_03
Patent number
US04816602

Reaction notes

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