4-Nitrophenol → 1-(3-Chloropropoxy)-4-nitrobenzene

HRID 1271411Notes

Reaction equation

HRID 1271411 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][CH2:20][Cl:21]>C(C(C)=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Nitrophenol (69.56 g, 0.5 mol), potassium carbonate (138.21 g, 1 mol) and 1-bromo-3-chloro propane (236.16 g, 1.5 mol) are refluxed in methyl ethyl ketone (800 ml) for 24 h. After filtration solvents are removed, the residue dissolved in ethyl acetate (1000 ml) and washed with NaOH (1M, 150 ml) and water (2×200 ml). Drying over sodium sulfate and concentration in vacuo yields 1-(3-Chloro-propoxy)-4-nitro-benzene as a yellow liquid.

Workup

  1. filtrationAfter filtration solvents
  2. customare removed
  3. dissolutionthe residue dissolved in ethyl acetate (1000 ml)
  4. washwashed with NaOH (1M, 150 ml) and water (2×200 ml)
  5. dry with materialDrying over sodium sulfate and concentration in vacuo

Sources & evidence

ORD record
ord-69133207926749428fb32b237058adde
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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