Nitric Acid → Methyl 3-hydroxy-4-methoxy-2-nitrobenzoate

HRID 1095782Notes

Reaction equation

HRID 1095782 reaction equation
[N+:1]([O-:4])(O)=[O:2].[OH:5][C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10]>C(O)(=O)C>[OH:5][C:6]1[C:7]([N+:1]([O-:4])=[O:2])=[C:8]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 59268115Methyl 3-hydroxy-4-methoxy-2-nitrobenzoateYield 27.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Nitric acid (95%, 42 g, 0.62 mol) was added dropwise (internal temperature kept below 5° C.) to a solution of methyl 3-hydroxy-4-methoxybenzoate (96.5%, 100 g, 0.53 mol) and acetic acid (250 mL) at 0° C. After 10 min at 0° C., a large amount of precipitate had formed and was collected by filtration. The filter cake was washed with water (100 mL×2), and then the crude product was recrystallized from methanol (40 mL) to give 33 g of methyl 3-hydroxy-4-methoxy-2-nitrobenzoate as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.64 (s, 1H), 7.49 (d, 1H), 7.22 (d, 1H), 3.93 (s, 3H), 3.76 (s, 3H); MS (ESI): 227.9.

Workup

  1. customa large amount of precipitate had formed
  2. filtrationwas collected by filtration
  3. washThe filter cake was washed with water (100 mL×2)
  4. customthe crude product was recrystallized from methanol (40 mL)

Sources & evidence

ORD record
ord-14b9d4e8b664451992dc8426c75e6c6d
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

Loading…