Water → HCID 23130247, compound

HRID 417282Notes

Reaction equation

HRID 417282 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[H-].[Na+].I[CH2:18][CH3:19].O>CN(C=O)C>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 23130247HCID 23130247, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Step A To a solution of methyl 3-hydroxy-4-nitrobenzoate (Aldrich) (3 g, 15.2 mmol) in anhydrous DMF (25 mL) were added NaH (Aldrich, 60%) (0.91 g, 22.8 mmol) and iodoethane (2.61 g, 16.7 mmol) sequentially. The reaction mixture was stirred at room temperature for 2 h. Water was added. The mixture was extracted with ethyl acetate. The organic extract was washed with water, brine, dried over MgSO4, and concentrated to give methyl 3-ethoxy-4-nitrobenzoate as a light yellow solid (1.0 g, 29%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79f4a2403f9844ceaf5ad9003d9009b9
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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