Sodium Hydroxide → 1,3-Dichloro-5-ethynylbenzene

HRID 1906505Notes

Reaction equation

HRID 1906505 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10]C(C)(O)C)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 138235464-(3,5-Dichloro-phenyl)-2-methyl-but-3-yn-2-ol

Product 1

HCID 138235471,3-Dichloro-5-ethynylbenzeneYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 7.95 g (0.0655 mole) of 1-(3,5-dichlorophenyl)-3-methyl-1-butyn-3-ol and 30 g of sodium hydroxide in 150 ml of dry toluene was heated to reflux with stirring for 3.5 hours. The toluene was removed in vacuo to yield a brown solid residue. The residue was triturated with hexane and the resulting hexane solution washed with aqueous sodium thiosulfate solution. The hexane layer was separated and evaporated in vacuo to yield the crude product. Recrystallization from hexane yielded 4.15 g of pure product, mp 80°-81.5° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customThe toluene was removed in vacuo
  4. customto yield a brown solid residue
  5. customThe residue was triturated with hexane
  6. washthe resulting hexane solution washed with aqueous sodium thiosulfate solution
  7. customThe hexane layer was separated
  8. customevaporated in vacuo
  9. customto yield the crude product
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-5dee07a4a24d4d1fb649d96ca34c2741
Source dataset
uspto-grants-1987_03
Patent number
US04652584

Reaction notes

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