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

HRID 1280205

Reaction equation

HRID 1280205 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([Cl:25])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][C:12](=O)[CH3:13].Cl.[C:27]([O:31][NH2:32])([CH3:30])([CH3:29])[CH3:28].Cl>N1C=CC=CC=1>[C:27]([O:31][N:32]=[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:18][C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])=[CH:16][C:15]=1[Cl:25])[CH3:13])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 184302155-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone

Product 1

HCID 543189495-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloximeYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.43 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone and 10 ml of pyridine was added 0.15 g of O-tert-butylhydroxylamine hydrochloride. After stirring at room temperature for 24 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, which afforded 0.45 g (yield, 90%) of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloxime, nD25.5 1.5170.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d4ce885b655544fc8d7317b6ce089c30
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Linked notes

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