Hydrochloric Acid → HCID 54061875, compound

HRID 1280220Notes

Reaction equation

HRID 1280220 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])[CH:18]=[C:17]([Cl:27])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.Cl.[CH2:29]([O:31][NH2:32])[CH3:30].Cl>N1C=CC=CC=1>[CH2:29]([O:31][N:32]=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:20][C:19]([O:21][CH2:22][CH:23]=[C:24]([Cl:26])[Cl:25])=[CH:18][C:17]=2[Cl:27])[CH:10]=1)[CH3:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 76850O-ethylhydroxylamine hydrochlorideHCID 18430013HCID 18430013, compound

Product 1

HCID 54061875HCID 54061875, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.21 g of 3-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde and 10 ml of pyridine was added 0.09 g of O-ethylhydroxylamine 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 0.21 g (yield, 92%) of 3-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde O-ethyloxime, m.p., 42.6° C.

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-3b6582a6f5a24af1bc0b8ac57bdf7aeb
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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