Citric Acid → HCID 53706633, compound

HRID 1280228Notes

Reaction equation

HRID 1280228 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][C:4](=O)[CH3:5].Cl.[Cl:9][C:10]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:21]=[C:20]([Cl:30])[C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][NH2:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[Cl:9][C:10]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:21]=[C:20]([Cl:30])[C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][N:19]=[C:4]([CH2:3][CH:2]([CH3:7])[CH3:1])[CH3:5]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 7909Methyl Isobutyl KetoneHCID 18429823HCID 18429823, compound

Product 1

HCID 53706633HCID 53706633, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.10 g of 4-methyl-2-pentanone and 5 ml of pyridine was added 0.40 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 0.42 g (yield, 95.4%) of 4-methyl-2-pentanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime, nD24.5 1.5230.

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-ba75860d7d3a4a83aa106cde400c2136
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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