Water → 4-Methoxy-3-(2-methoxyethoxy)nitrobenzene

HRID 393603

Reaction equation

HRID 393603 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].[CH3:13][O:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.[I-].[K+]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[O:12][CH2:16][CH2:15][O:14][CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenolHCID 809722-Bromoethyl methyl ether

Product 1

HCID 107993054-Methoxy-3-(2-methoxyethoxy)nitrobenzeneYield 98%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-methoxy-5-nitrophenol (6 g, 35 mmol), 2-bromoethyl methyl ether (4 ml, 40 mmol), potassium carbonate (5.8 g, 40 mmol) and potassium iodide (0.5 g) in DMF (50 ml) was heated at 80° C. for 1 hour. The mixture was allowed to cool and poured into water (400 ml). The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give 4-methoxy-3-(2-methoxyethoxy)nitrobenzene (7.75 g, 98%).

Workup

  1. temperatureto cool
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-559672ba6c0c414dbf5e79a7e1c891f3
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Linked notes

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