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

HRID 2305023Notes

Reaction equation

HRID 2305023 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=O.Cl.[C:26]([O:30][NH2:31])([CH3:29])([CH3:28])[CH3:27].Cl>N1C=CC=CC=1>[C:26]([O:30][N:31]=[CH:12][CH2:11][O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[C:14]([Cl:24])=[CH:15][C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])=[CH:17][C:2]=1[Cl:1])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 540452085-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde

Product 1

HCID 544557595-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-tert-butyloximeYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.42 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde 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 0.45 g (yield, 92%) of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-tert-butyloxime, nD25.2 1.5185.

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-b56e14137ad34442b25d763b25bff4e2
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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