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

HRID 1195018Notes

Reaction equation

HRID 1195018 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+]>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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15919150HCID 15919150, compound

Product 1

HCID 159191511,6-Dichloro-3,3,6-trimethylhept-1-yne

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.68 g of 1,1,1,6-tetrachloro-3,3,6-trimethylheptane is combined in 4 ml of dichloromethane with 10 ml of 40% aqueous sodium hydroxide solution and 0.52 g of "Aliquat" 336, and heated under reflux for 17 hours. Then the reaction mixture is allowed to cool, combined with 20 ml of dichloromethane, the organic phase is separated, washed with water, and dried over calcium chloride. The solution is then concentrated under vacuum, yielding 1,6-dichloro-3,3,6-trimethyl-1-heptyne as an oily crude product.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 17 hours
  3. temperatureto cool
  4. customthe organic phase is separated
  5. washwashed with water
  6. dry with materialdried over calcium chloride
  7. concentrationThe solution is then concentrated under vacuum

Sources & evidence

ORD record
ord-11065c1122ce4c85a7558cddbf045584
Source dataset
uspto-grants-1989_03
Patent number
US04816602

Reaction notes

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