Hydrochloric Acid → HCID 54152236, compound

HRID 1280223Notes

Reaction equation

HRID 1280223 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][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1.Cl.[C:28]([O:32][NH2:33])([CH3:31])([CH3:30])[CH3:29].Cl>N1C=CC=CC=1>[C:28]([O:32][N:33]=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([CH2:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:19][C:18]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])=[CH:17][C:16]=2[Cl:26])=[CH:9][CH:10]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 18429585HCID 18429585, compound

Product 1

HCID 54152236HCID 54152236, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.43 g of 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl)benzaldehyde and 5 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 to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 0.38 g (yield, 75%) of 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl)benzaldehyde O-tert-butyloxime, nD25.5 1.5673.

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-b1d2a94e90b0432dbb144f40fdb69acf
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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