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

HRID 401611

Reaction equation

HRID 401611 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-5b8c2a2be6f74fb8b7a7f609036c07b5
Source dataset
uspto-grants-2014_06
Patent number
US08741942B2

Linked notes

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