Water → 4-Methyl-1-nitro-2-[2-(2-nitrophenoxy)ethoxy]benzene

HRID 1852365Notes

Reaction equation

HRID 1852365 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12].[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([OH:21])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[C:19]([O:21][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-:13])=[O:12])[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 127886-Nitro-m-cresolHCID 43624871-(2-chloroethoxy)-2-nitrobenzene

Product 1

HCID 27630554-Methyl-1-nitro-2-[2-(2-nitrophenoxy)ethoxy]benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-(2-Chloro-ethoxy)-2-nitro-benzene (116 g) and 5-methyl-2-nitro-phenol (88 g) were dissolved in 500 ml DMF and was stirred for 4 h at 90-110° C. after careful addition of 160 g potassium carbonate. The reaction mixture was poured in a mixture of crushed ice and water (8 l) which was vigorously stirred. The residue was filtered off, washed several times with water and dried. The crude product was suspended in methanol and the pale yellow residue was again filtered off, washed with methanol and dried. Yield: 150-165 g.

Workup

  1. stirringwas vigorously stirred
  2. filtrationThe residue was filtered off
  3. washwashed several times with water
  4. customdried
  5. filtrationthe pale yellow residue was again filtered off
  6. washwashed with methanol
  7. customdried

Sources & evidence

ORD record
ord-22c6d06fd49b4326b2ec6360d3ecb503
Source dataset
uspto-grants-2015_02
Patent number
US08962338B2

Reaction notes

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