Water → Benzoic acid, 3-methoxy-2-nitro-, methyl ester

HRID 576325

Reaction equation

HRID 576325 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:15]([O-])([O-])=O.[K+].[K+].CI.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH3:15])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 786323-Methoxy-2-nitrobenzoic acid

Product 1

HCID 79195Benzoic acid, 3-methoxy-2-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-methoxy-2-nitrobenzoic acid (25.0 g, 126 mmol) and K2CO3 (35.0 g, 253 mmol) in DMF (126 mL) was added MeI (15.8 mL, 253 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. To the mixture was poured the water (200 mL) and then stirred at 5° C. for 30 min. The precipitated solid was collected by filtration, washed with water and hexane. The solid was dried under reduced pressure to afford the compound 52 in a crude form (26.2 g, 98%) as a white solid.

Workup

  1. stirringstirred at 5° C. for 30 min
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water and hexane
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-fb38c9e1c3204998875316fa067af5e4
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Linked notes

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