4-Chlorophenol → HCID 13727461, compound

HRID 1761471Notes

Reaction equation

HRID 1761471 reaction equation
Cl[CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[C:5]#[CH:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[C:5]#[CH:6])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 13727460HCID 13727460, compound

Product 1

HCID 13727461HCID 13727461, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 98 g (0.67 mole) of 1-chloro-3,3-dimethyl-pent-4-in-2-one is added dropwise, with stirring, to a boiling mixture of 86.1 g (0.67 mole) of 4-chlorophenol and 92.5 g (o.67 mole) of potassium carbonate powder in 500 ml of acetone. After five hours the mixture is filtered, the filtrate is evaporated, the residue is taken up in 250 ml of methylene chloride and this solution is washed with 200 ml of 1N sodium hydroxide solution and 200 ml of water. After the solvent has been distilled off, 149 g (that is to say 94% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-pent-4-in-2-one are obtained as a colorless viscous oil, which upon standing solidifies to crystals.

Workup

  1. filtrationAfter five hours the mixture is filtered
  2. customthe filtrate is evaporated
  3. washthis solution is washed with 200 ml of 1N sodium hydroxide solution and 200 ml of water
  4. distillationAfter the solvent has been distilled off

Sources & evidence

ORD record
ord-06d389de231043d0851d5a731d8b6cfc
Source dataset
uspto-grants-1989_05
Patent number
US04826865

Reaction notes

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