Hydrochloric Acid → HCID 54520900, compound

HRID 1280196Notes

Reaction equation

HRID 1280196 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=O.Cl.[Cl:25][C:26]([Cl:31])=[CH:27][CH2:28][O:29][NH2:30].Cl>N1C=CC=CC=1>[Cl:25][C:26]([Cl:31])=[CH:27][CH2:28][O:29][N:30]=[CH:11][CH2:10][O:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[C:13]([Cl:23])=[CH:14][C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:21])[Cl:22])=[CH:16][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18429391HCID 18429391, compoundHCID 538269084-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde

Product 1

HCID 54520900HCID 54520900, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.37 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde and 10 ml of pyridine was added 0.20 g of O-(3,3-dichloro-2-propenyl)hydroxylamine 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 to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 0.39 g (yield, 74%) of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-(3,3-dichloro-2-propenyl)oxime, nD24.0 1.5489.

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-9d8b27f0f8ce498f8ab656304297250d
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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