Iodoethane → HCID 23130247, compound

HRID 2114162Notes

Reaction equation

HRID 2114162 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:7]([O:9][CH3:10])=[O:8].[CH2:17](I)[CH3:18].[Cl-].[NH4+]>CN(C)C=O>[CH2:17]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:7]([O:9][CH3:10])=[O:8])[CH3:18]

Participants

6

Reactant 4

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

Product 1

HCID 23130247HCID 23130247, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at 60° C. overnight
  3. temperatureThe reaction solution was cooled down to room temperature
  4. extractionextracted with ethyl acetate-tetrahydrofuran
  5. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto yield a solid
  9. washThe solid was washed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-52953b6b54814c22a489788736b71c01
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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