Chloroacetone → 2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxyacetone

HRID 2305071Notes

Reaction equation

HRID 2305071 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[CH2:23][C:24](=[O:26])[CH3:25]>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][CH2:23][C:24](=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 184299252,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxyacetone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 8.64 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 4.98 g of potassium carbonate, 3.36 g of chloroacetone, and 50 ml of N,N-dimethylformamide were placed in a reaction vessel. After stirring at room temperature for 24 hours, the reaction mixture was filtered. The filtrate was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated, which afforded 10.12 g (yield, 98%) of (2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxyacetone, m.p., 83.8° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was poured into diluted hydrochloric acid
  3. extractionextracted twice with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customwhich afforded

Sources & evidence

ORD record
ord-ca5b9323e640472dbb0c05eb1e933757
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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