Potassium Iodide → HCID 66755899, compound

HRID 1642010Notes

Reaction equation

HRID 1642010 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:16][O:17][CH2:18][CH2:19]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:16][O:17][CH2:18][CH2:19][O:1][C:2]1[C:3]([CH3:15])=[C:4]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 66756872HCID 66756872, compound

Product 1

HCID 66755899HCID 66755899, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 3-hydroxy-2-methyl-4-nitrobenzoate (1.55 g) and 2-chloroethyl methyl ether (1.8 g) were dissolved in anhydrous DMF (20 mL), and potassium carbonate (1.25 g) and potassium iodide (300 mg) were added, followed by stirring at 90° C. for 20 hours. To the reaction mixture, ethyl acetate (200 mL) was added, followed by washing twice with saturated brine. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain methyl 3-(2-methoxyethoxy)-2-methyl-4-nitrobenzoate (2.1 g) as pale yellow solid.

Workup

  1. washby washing twice with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3f7af35299084f24811a0de6f15605ab
Source dataset
uspto-grants-2012_02
Patent number
US08119569B2

Reaction notes

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