4-Chlorophenol → 3,5-Dichloro-4-(4-(4-chlorophenoxy) butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 363071Notes

Reaction equation

HRID 363071 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:5]=[C:6]([Cl:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:28][C:25]1[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 222571451-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-4-bromobutane

Product 1

HCID 544206313,5-Dichloro-4-(4-(4-chlorophenoxy) butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.61 g of 3,5-dichloro-4-(4-bromobutyloxy)-1-(3,3-dichloro-2-propenyloxy) benzene, 0.19 g of 4-chlorophenol, 0.22 g of potassium carbonate and 20 ml of N,N-dimethylformamide was stirred at room temperature. After 7 hours, the reaction mixture was poured into ice-water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.54 g of 3,5-dichloro-4-(4-(4-chlorophenoxy) butyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (59% yield), m.p. 54.5° C.

Workup

  1. extractionextracted twice with 50 ml of diethyl ether
  2. washThe combined ether layer was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product

Sources & evidence

ORD record
ord-4d1a3dd51d4f49dcbef73e92754788aa
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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