Citric Acid → HCID 54135716, compound

HRID 1280227Notes

Reaction equation

HRID 1280227 reaction equation
[CH3:1][C:2]([CH3:6])([CH3:5])[CH:3]=O.Cl.[Cl:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][NH2:18].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[Cl:8][C:9]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:10]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][N:18]=[CH:3][C:2]([CH3:6])([CH3:5])[CH3:1]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 12417PivalaldehydeHCID 18429823HCID 18429823, compound

Product 1

HCID 54135716HCID 54135716, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.07 g of trimethylacetaldehyde and 5 ml of pyridine was added 0.30 g of O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)hydroxylamine hydrochloride. After stirring at room temperature for 1 hour, the reaction mixture was poured into 5% aqueous citric acid solution, and extracted twice with ethyl acetate. The ethyl acetate 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 0.31 g (yield, 96.8%) of trimethylacetaldehyde O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime, nD23.0 1.5178.

Workup

  1. extractionextracted twice with ethyl acetate
  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-4b68f3ac78cd44459acd9c040ff39ff5
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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