Citric Acid → 4-(trifluoromethyl)benzaldehyde O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime

HRID 1280225Notes

Reaction equation

HRID 1280225 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.Cl.[Cl:14][C:15]1[CH:27]=[C:26]([O:28][CH2:29][CH:30]=[C:31]([Cl:33])[Cl:32])[CH:25]=[C:24]([Cl:34])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][NH2:23].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>N1C=CC=CC=1>[Cl:14][C:15]1[CH:27]=[C:26]([O:28][CH2:29][CH:30]=[C:31]([Cl:33])[Cl:32])[CH:25]=[C:24]([Cl:34])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][N:23]=[CH:7][C:6]1[CH:9]=[CH:10][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 679964-(Trifluoromethyl)benzaldehydeHCID 18429772O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)hydroxylamine hydrochloride

Product 1

HCID 538001354-(trifluoromethyl)benzaldehyde O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oximeYield 95.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 0.14 g of 4-(trifluoromethyl)benzaldehyde and 10 ml of pyridine was added 0.30 g of O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)hydroxylamine hydrochloride. After stirring at room temperature for 1 hour, the reaction mixture was poured into5% 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 0.37 g (yield, 95.6%) of 4-(trifluoromethyl)benzaldehyde O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime, nD21.0 1.5387.

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-4db5e12402fe4a5e910febf6d3685267
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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