2-Nitrophenol → 1-(3-Methoxypropoxy)-2-nitrobenzene

HRID 1176210Notes

Reaction equation

HRID 1176210 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Cl[CH2:12][CH2:13][CH2:14][O:15][CH3:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 1189271-Chloro-3-methoxypropane

Product 1

HCID 685007031-(3-Methoxypropoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2.00 g of 2-nitrophenol, 1.72 g of 1-chloro-3-methoxypropane and 3.04 g potassium carbonate in 20 ml of N,N-dimethylformamide is stirred at reflux over 23 hours. The reaction mixture is concentrated by evaporation. The residue is partitioned between ethyl acetate and a 9:1 water/brine mixture. The water phase is extracted using ethyl acetate (2×). The organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.33 (1:2 EtOAc-heptane); Rt=4.08.

Workup

  1. temperatureat reflux over 23 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customThe residue is partitioned between ethyl acetate
  4. extractionThe water phase is extracted
  5. washThe organic phases are washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-b97f57bc11064e4984ae583d86c7aa7f
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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