Hydrochloric Acid → (2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-acetone O-(3-(5-trifluoromethyl-2-pyridyloxy)propyl)oxime

HRID 2305040Notes

Reaction equation

HRID 2305040 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:10]=[C:9]([Cl:19])[C:3]=1[O:4][CH2:5][C:6](=O)[CH3:7].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][NH2:33])=[N:26][CH:27]=1.[Cl-].[NH+]1C=CC=CC=1.Cl>N1C=CC=CC=1>[F:34][C:21]([F:20])([F:35])[C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][CH2:31][O:32][N:33]=[C:6]([CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:12][C:11]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])=[CH:10][C:9]=2[Cl:19])[CH3:7])=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69401Einecs 211-027-4HCID 184298142-[3-(Aminooxy)propoxy]-5-(trifluoromethyl)pyridineHCID 184299252,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxyacetone

Product 1

HCID 54175010(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-acetone O-(3-(5-trifluoromethyl-2-pyridyloxy)propyl)oximeYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.34 g of (2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)-phenoxy)acetone, 0.24 g of O-(3-(5-trifluoromethyl-2-pyridyloxy)propyl)-hydroxylamine, 0.14 g of pyridinium chloride, and 10 ml of pyridine was stirred at room temperature for 2 hours. The reaction mixture 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 to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.40 g (yield, 71%) of (2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)-acetone O-(3-(5-trifluoromethyl-2-pyridyloxy)propyl)oxime, nD23.0 1.5310.

Workup

  1. extractionextracted twice with diethyl ether
  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-feac6019b3014532a402abde22a4252c
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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