Hydrochloric Acid → HCID 53909295, compound

HRID 2305035Notes

Reaction equation

HRID 2305035 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]([CH2:41][CH3:42])[CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]OS(C)(=O)=O)([CH3:25])([CH3:24])[CH3:23].Cl>CN(C)C=O>[C:22]([O:26][N:27]=[C:28]([CH2:41][CH3:42])[CH2:29][O:30][CH2:31][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])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 53815860HCID 53815860, compound

Product 1

HCID 53909295HCID 53909295, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

First, 0.46 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.25 g of potassium carbonate, 0.58 g of 1-(5-(methanesulfonyloxy)pentyloxy)-2-butanone O-tert-butyloxime, and 15 ml of N,N-dimethylformamide are placed in a reaction vessel. After stirring at 55° C. to 60° C. for 24 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 0.69 g (yield, 84%) of 1-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxy)-2-butanone O-tert-butyloxime, nD23.4 1.5140.

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-d91effcd9c924da9b0bb6ad3c1a4501e
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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