Ethyl Acetate → Methyl {o-{5-[2-chloro-4-(methylsulfinyl)phenoxy]-2-nitrophenoxy}phenoxy}acetate

HRID 21526Notes

Reaction equation

HRID 21526 reaction equation
[Cl:1][C:2]1[CH:30]=[C:29]([S:31][CH3:32])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:24]([O-:26])=[O:25])=[C:9]([CH:23]=1)[O:10][C:11]1[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=1[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].ClC1C=C(C=CC=1)C(OO)=[O:38].C(OCC)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:30]=[C:29]([S:31]([CH3:32])=[O:38])[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:24]([O-:26])=[O:25])=[C:9]([CH:23]=1)[O:10][C:11]1[CH:22]=[CH:21][CH:20]=[CH:19][C:12]=1[O:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 53873458HCID 53873458, compound

Product 1

HCID 54257755Methyl {o-{5-[2-chloro-4-(methylsulfinyl)phenoxy]-2-nitrophenoxy}phenoxy}acetateYield 58.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl {o-{5-[2-chloro-4-(methylthio)phenoxy]-2-nitrophenoxy}phenoxy}acetate (4.30 g, 0.009 mol) in methylene chloride is cooled to 0° C. and treated with 3-chloroperoxybenzoic acid (1.73 g, 0.010 mol). The reaction mixture is warmed to room temperature, stirred overnight, quenched with triethylamine (1.4 mL) and concentrated in vacuo. The residue is dissolved into ethyl acetate and the organic solution is washed sequentially with water and 2 N hydrochloric acid, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an amber oil. Column chromatography of the oil using silica gel and ethyl acetate gives the title product as an amber oil (2.6 g) which is identified by NMR spectral analyses.

Workup

  1. customquenched with triethylamine (1.4 mL)
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved into ethyl acetate
  4. washthe organic solution is washed sequentially with water and 2 N hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an amber oil

Sources & evidence

ORD record
ord-a8b9a9641653481db5a68fae31d5cdd0
Source dataset
uspto-grants-1995_06
Patent number
US05424280

Reaction notes

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