Hydrochloric Acid → HCID 53797134, compound

HRID 1280198Notes

Reaction equation

HRID 1280198 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:20])[Cl:19])[CH:12]=[C:11]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8]C=O.Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24].Cl.N1C=CC=C[CH:31]=1>>[C:23]([O:27][N:28]=[CH:8][CH2:7][CH2:6][CH:5]([O:4][C:3]1[C:11]([Cl:21])=[CH:12][C:13]([O:15][CH2:16][CH:17]=[C:18]([Cl:19])[Cl:20])=[CH:14][C:2]=1[Cl:1])[CH3:31])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 18430083HCID 18430083, compound

Product 1

HCID 53797134HCID 53797134, compoundYield 50%

Procedure

To a mixture of 0.37 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal and 10 ml of pyridine was added 0.13 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 0.22 g (yield, 50%) of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal O-tert-butyloxime, nD25.2 1.5275.

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-b965019e8b1344059eb2978e6f30d2da
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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