Iodoethane → HCID 57663522, compound

HRID 2105846Notes

Reaction equation

HRID 2105846 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[OH:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14].[C:23](OCC)(=O)[CH3:24]>CC(=O)CC>[CH2:23]([O:10][C:11]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH2:8][CH3:9])=[O:14])[CH3:24]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 692664-Nitrosalicylic acid

Product 1

HCID 57663522HCID 57663522, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (60.4 g, 437 mmol) and iodoethane (17.6 mL, 218.4 mmol) were added to a mechanically stirred solution of 2-hydroxy-4-nitro-benzoic acid (10.0 g, 54.6 mmol) in 2-butanone (165 mL). The resulting mixture was heated in an 80° C. oil bath for 16 h and then allowed to cool. TLC (20% ethyl acetate in hexanes) showed consumption of starting material. The reaction mixture was concentrated to dryness, and the residue was taken up in ethyl acetate and washed three times with a saturated solution of sodium thiosulfate, dried over magnesium sulfate and concentrated to give ethyl 2-ethoxy-4-nitro-benzoate as a yellow solid (12.7 g, 97%). LC-MS: 240.1 [(M+H)+].

Workup

  1. temperatureto cool
  2. customconsumption of starting material
  3. concentrationThe reaction mixture was concentrated to dryness
  4. washwashed three times with a saturated solution of sodium thiosulfate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9f4ed454eca44608a83a7dcd57c5672b
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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