4-Chlorophenol → 1-Chloro-4-[(5,5-dichloro-3,3-dimethylpent-4-en-1-yl)oxy]benzene

HRID 2413055Notes

Reaction equation

HRID 2413055 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]([Cl:18])=[CH:11][C:12]([CH3:17])([CH3:16])[CH2:13][CH2:14]Cl.C(=O)([O-])[O-].[K+].[K+]>COCCOCCOC.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][CH2:13][C:12]([CH3:17])([CH3:16])[CH:11]=[C:10]([Cl:18])[Cl:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 155843271,1,5-Trichloro-3,3-dimethylpent-1-ene

Product 1

HCID 132414221-Chloro-4-[(5,5-dichloro-3,3-dimethylpent-4-en-1-yl)oxy]benzeneYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8150DiglymeSolvent

Procedure

128 g (1 mol) of 4-chlorophenol, 201 g (1 mol) of 1,1,5-trichloro-3,3-dimethyl-1-pentene (II) and 138 g (1 mol) of potassium carbonate in 1 liter of diethylene glycol dimethyl ether are heated under reflux for 10 hours. The mixture is then diluted with methylene chloride and extracted by shaking several times with water. The organic phase is freed of solvent on a rotary evaporator and then distilled at a boiling point of 135°-140° C./0.1 mbar. 252 g (0.86 mol, which is 86% of theory) of 5-(4-chlorophenoxy)-1,1-dichloro-3,3-dimethyl-1-pentene are obtained.

Workup

  1. temperatureunder reflux for 10 hours
  2. extractionextracted
  3. customThe organic phase is freed of solvent on a rotary evaporator
  4. distillationdistilled at a boiling point of 135°-140° C./0.1 mbar

Sources & evidence

ORD record
ord-ac6721fb313b425794815e738f6bb3d3
Source dataset
uspto-grants-1985_01
Patent number
US04495370

Reaction notes

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