Hydrochloric Acid → HCID 53890480, compound

HRID 2305036Notes

Reaction equation

HRID 2305036 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+].[C:22]([O:26][N:27]=[C:28]([CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35]OS(C)(=O)=O)[CH3:29])([CH3:25])([CH3:24])[CH3:23].Cl>CN(C)C=O>[C:22]([O:26][N:27]=[C:28]([CH2:30][O:31][CH2:32][CH2:33][CH2:34][CH2:35][O:15][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH2:9][CH:10]=[C:11]([Cl:13])[Cl:12])=[CH:5][C:4]=1[Cl:14])[CH3:29])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 53746133HCID 53746133, compound

Product 1

HCID 53890480HCID 53890480, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

First, 0.55 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.30 g of potassium carbonate, 0.59 g of 4-(methanesulfonyloxy)butyloxyacetone O-tert-butyloxime, and 10 ml of N,N-dimethylformamide are placed in a reaction vessel. After stirring at 60° C. for 6 hours, the reaction mixture is poured into diluted hydrochloric acid, and extracted twice with ethyl acetate. The ethyl acetate layers are combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product is subjected to silica gel chromatography, which affords 0.71 g (yield, 77%) of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-butyloxyacetone O-tert-butyloxime, nD25.0 1.5170.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product

Sources & evidence

ORD record
ord-ae8194da336c4a768425004c2dd62bf9
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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