Hydrochloric Acid → 1-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-oxime

HRID 2099931Notes

Reaction equation

HRID 2099931 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1.Cl.[N:31](OCCC(C)C)=[O:32].C(N(CC)CC)C>O1CCOCC1.O>[Cl:1][C:2]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([Cl:28])[Cl:27])[CH:20]=[C:19]([Cl:29])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[N:31][OH:32])[C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 8471TriethylamineHCID 866054261-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)propan-2-one

Product 1

HCID 866225881-(4-{3-[2,6-Dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-oxime

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2.0 g of 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)propan-2-one are introduced into 4 ml of HCl 5% in dioxane, then 0.6 g of isopentyl nitrite is added dropwise thereto. After 1 hour's stirring at room temperature, 0.8 ml of triethylamine is added. The reaction mixture is poured into water and extracted with ethyl acetate. After concentration of the organic phase and purification over silica gel, 1-(4-{3-[2,6-dichloro-4-(3,3-dichloro-allyloxy)-phenoxy]-propoxy}-phenyl)-propane-1,2-dione 1-oxime is obtained. 1H-NMR (CDCl3) 300 MHz: 2.30 (m, 2H), 2.51 (s, 3H), 4.16 (t, 2H), 4.30 (t, 2H), 4.58 (d, 2H), 6.11 (t, 1H), 6.84 (s, 2H), 6.98 (d, 2H), 7.34 (d, 2H), 8.30 (s, 1H)

Workup

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

Sources & evidence

ORD record
ord-c6e8e5ec433a42c78103d3a0b63819fd
Source dataset
uspto-grants-2009_08
Patent number
US07569727B2

Reaction notes

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