Iodoethane → HCID 23130247, compound

HRID 1864956Notes

Reaction equation

HRID 1864956 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([OH:15])[CH:7]=1.[CH2:17](I)[CH3:18].[Cl-].[NH4+]>CN(C)C=O>[CH3:3][O:4][C:5](=[O:16])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:15][CH2:17][CH3:18])[CH:7]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 23130247HCID 23130247, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% mineral oil: 1.20 g) in dimethylformamide (50 mL) was added 3-hydroxy-4-nitrobenzoic acid methyl ester (4.93 g) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. After addition of ethyl iodide (4.4 g), the solution was stirred at 60° C. overnight, cooled down to room temperature, poured into saturated aqueous ammonium chloride, and extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated aqueous ammonium chloride and saturated brine, dried over sodium sulfate and concentrated to give a solid, which was washed with ethyl acetate-hexane to afford 3-ethoxy-4-nitrobenzoic acid methyl ester (3.30 g) as a pale yellow solid.

Workup

  1. temperaturecooling
  2. stirringthe solution was stirred at 60° C. overnight
  3. temperaturecooled down to room temperature
  4. extractionextracted with ethyl acetate-tetrahydrofuran
  5. washThe organic layer was washed with saturated aqueous ammonium chloride and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a solid, which
  9. washwas washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-23c6b2eb04dc4443bbf7daad51d55436
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

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