Phenol → 1-(2-Methoxy-ethoxy)-3-methyl-2-nitrobenzene

HRID 1098622

Reaction equation

HRID 1098622 reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C1(O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][O:26][CH2:27][CH2:28]Br>CN(C=O)C.O>[CH3:25][O:26][CH2:27][CH2:28][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

7

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 210263-Methyl-2-nitrophenolHCID 809722-Bromoethyl methyl ether

Product 1

HCID 128554961-(2-Methoxy-ethoxy)-3-methyl-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The required 1-(2-methoxy-ethoxy)-3-methyl-2-nitrobenzene was prepared from 3-methyl-2-nitrophenol. To a stirred solution of the phenol (2.0 g, 13.1 mmol) in DMF (65 mL) was added potassium carbonate (2.16 g, 15.7 mmol) and bromoethyl methyl ether (1.47 mL, 15.7 mmol) at room temperature. After the mixture was stirred at 50° C. for 48 h, water was added. The mixture was extracted with EtOAc (3×), washed with brine, dried over anhydrous MgSO4 filtered and evaporated. After chromatographic purification on silica gel, 1-(2-methoxy-ethoxy)-3-methyl-2-nitrobenzene was obtained in 85% yield (2.34 g). 1H NMR (500 MHz, CDCl3) δ 7.28 (1H, t, J=8.0 Hz), 6.89 (1H, d, J=9.0 Hz), 6.85 (1H, d, J=8.0 Hz), 4.19 (2H, t, J=4.5 Hz), 3.72 (2H, t, J=5.0 Hz), 3.41 (3H, s), 2.30 (3H, s).

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customAfter chromatographic purification on silica gel

Sources & evidence

ORD record
ord-fdcb500e371e41eea1b41b94dc63b6b8
Source dataset
uspto-grants-2012_03
Patent number
US08143300B2

Linked notes

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