Methyl iodide → Benzoic acid, 5-methoxy-2-methyl-3-nitro-, methyl ester

HRID 2208917Notes

Reaction equation

HRID 2208917 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5](C)=[C:6]([CH:10]=1)C(O)=O.[C:15](=O)([O-])[O-].[Na+].[Na+].CI.[C:23]([O:26][CH2:27]C)(=[O:25])[CH3:24]>CN(C=O)C.O>[CH3:15][O:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:6])=[C:24]([CH:10]=1)[C:23]([O:26][CH3:27])=[O:25]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 23009717HCID 23009717, compound

Product 1

HCID 53399479Benzoic acid, 5-methoxy-2-methyl-3-nitro-, methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-hydroxy-2-methyl-3-nitrobenzoic acid (1.50 g, 7.61 mmol) in DMF (15 mL) was added sodium carbonate (3.23 g, 30.5 mmol) and methyl iodide (1.88 mL, 30.5 mmol). The resulting reaction mixture was heated at 60° C. for 8 h. On completion, the reaction mixture was diluted with water and extraction was carried out using ethyl acetate. The combined organic layers were dried and concentrated under reduced pressure to give the crude title compound (1.7 g) which was used directly in the next step.

Workup

  1. customThe resulting reaction mixture
  2. customThe combined organic layers were dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5fa4c38e4e94694965a113c9df36cac
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…