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

HRID 1280248Notes

Reaction equation

HRID 1280248 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)phenoxy-acetone, 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-c616bd56477e4bb2a3bcb644c55d85d3
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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