Water → HCID 76608131, compound

HRID 2099929Notes

Reaction equation

HRID 2099929 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])[CH:21]=[C:20]([Cl:30])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][O:17][CH3:18])=[CH:11][CH:10]=1.Cl.[CH3:32][O:33][NH2:34].C([O-])(=O)C.[Na+].O>CO>[CH3:32][O:33][N:34]=[C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:23][C:22]([O:24][CH2:25][CH:26]=[C:27]([Cl:29])[Cl:28])=[CH:21][C:20]=2[Cl:30])=[CH:10][CH:11]=1)[CH2:16][O:17][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86602674HCID 86602674, compound

Product 1

HCID 76608131HCID 76608131, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

296 mg of 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-2-methoxy-ethanone, 56 mg of O-methylhydroxylamine hydrochloride and 55 mg of sodium acetate are stirred in 4 ml of methanol at room temperature for 24 hours. The reaction mixture is poured into water and extracted with ethyl acetate. After concentration of the organic phases and purification over silica gel, the title compound is obtained in the form of an E/Z mixture. 1H-NMR (CDCl3) 300 MHz: 2.30 (m, 2H), 3.32+3.46 (s+s, 3H), 3.93+3.99 (s+s, 3H), 4.18 (t, 2H), 4.29 (m, 2H), 4.53-4.61 (m, 4H), 6.11 (t, 1H), 6.83 (s, 2H), 6.91 (d, 2H), 7.62 (d, 2H)

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter concentration of the organic phases and purification over silica gel

Sources & evidence

ORD record
ord-885c4c28610949e79589db72dac97950
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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