Hydrochloric Acid → HCID 86584396, compound

HRID 2305025Notes

Reaction equation

HRID 2305025 reaction equation
[CH2:1]([C:3]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([CH2:24][CH3:25])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=O)[CH3:2].Cl.[NH2:27][OH:28].Cl>N1C=CC=CC=1>[CH2:1]([C:3]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([CH2:24][CH3:25])[C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=[N:27][OH:28])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 54234953HCID 54234953, compound

Product 1

HCID 86584396HCID 86584396, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.75 g of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde and 10 ml of pyridine was added 0.15 g of 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 0.67 g (yield, 75%) of 4-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde oxime, nD24.5 1.5278.

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-b1db3b0d9c564138a34af04ba9d364e1
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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