Methyl iodide → Methyl 3-methoxy-4-methyl-2-nitrobenzoate

HRID 1672478

Reaction equation

HRID 1672478 reaction equation
O[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:15]([O-])([O-])=O.[K+].[K+].CI.C(Cl)Cl.[CH3:26][OH:27]>CN(C=O)C.O>[CH3:26][O:27][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:15])=[O:6]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 813743-Hydroxy-4-methyl-2-nitrobenzoic acidHCID 21226129Dichloromethane methanol

Product 1

HCID 14543060Methyl 3-methoxy-4-methyl-2-nitrobenzoateYield 94.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxy-4-methyl-2-nitrobenzoic acid (365 g, 1.85 mol) in DMF (3280 mL) were added K2CO3 (524.4 g, 3.80 mol) and MeI (788 g, 5.55 mol) in one portion. Then the reaction mixture was stirred at room temperature overnight. TLC(CH2Cl2/MeOH=3:1) indicated the reaction was complete. Water (9 L) was added to the reaction mixture and the mixture was extracted with EtOAc (3 L×2). The combined organic layers were washed with 1 N aq. NaOH (1 L×2) and brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound (395 g, 94.7%) as a light yellow solid.

Workup

  1. extractionthe mixture was extracted with EtOAc (3 L×2)
  2. washThe combined organic layers were washed with 1 N aq. NaOH (1 L×2) and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc9a8d433be54c0487e702831b7e51a7
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Linked notes

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