Sulfuric Acid → 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloxime

HRID 2305038Notes

Reaction equation

HRID 2305038 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])[CH:17]=[C:16]([Cl:26])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12](=[N:14][OH:15])[CH3:13].S(=O)(=O)(O)O.[CH2:32]=[C:33]([CH3:35])[CH3:34].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:33]([O:15][N:14]=[C:12]([CH2:11][O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[C:2]([Cl:1])=[CH:19][C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])=[CH:17][C:16]=1[Cl:26])[CH3:13])([CH3:35])([CH3:34])[CH3:32]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 865843985-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone oxime

Product 1

HCID 543189495-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloxime

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

First, 0.45 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone oxime, 0.3 ml of concentrated sulfuric acid, and 10 ml of toluene are placed in a reaction vessel, into which isobutene gas is blown with stirring under ice cooling, and the mixture is further stirred at room temperature. After completion of the reaction, the reaction mixture is slowly poured into a saturated aqueous sodium hydrogencarbonate solution, and extracted twice with diethyl ether. The diethyl ether 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 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloxime.

Workup

  1. stirringthe mixture is further stirred at room temperature
  2. customAfter completion of the reaction
  3. extractionextracted twice with diethyl ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto give a crude product

Sources & evidence

ORD record
ord-7cc2c08c04e849418407256ccbbc4748
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

Loading…