Potassium Carbonate → HCID 54282554, compound

HRID 363063Notes

Reaction equation

HRID 363063 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[OH:15].C(=O)([O-])[O-].[K+].[K+].[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])[CH:5]=[C:4]([Cl:14])[C:3]=1[O:15][CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([Cl:22])[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12103m,alpha-DichlorotolueneHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 54282554HCID 54282554, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.51 g of 2,6-dichloro-4-(3,3,-dichloro-2-propenyloxy)phenol, 0.27 g of potassium carbonate and 20 ml of N,N-dimethylformamide was added dropwise a solution of 0.29 g of m-chlorobenzyl chloride dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 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 0.50 g of 3,5-dichloro-4-(3-chlorobenzyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene (69% yield), m.p. 87.0° C.

Workup

  1. stirringAfter stirring at room temperature for 7 hours
  2. extractionextracted twice with 50 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-2d676d34764f4e419fd58c7ef19609c6
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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