Nitric Acid → HCID 22663227, compound

HRID 392226Notes

Reaction equation

HRID 392226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[N+:14]([O-])([OH:16])=[O:15].O>C(O)(=O)C>[OH:13][C:5]1[C:4]([N+:14]([O-:16])=[O:15])=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 962WaterHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 22663227HCID 22663227, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of methyl 4-methoxysalicylate (50 g) in glacial acetic acid (700 ml) was treated dropwise with concentrated nitric acid (50 ml) over 15 minutes. After stirring for 2 hours, then standing at room temperature for 18 hours, the mixture was treated with a further aliquot of concentrated nitric acid (10 ml) then stirred for 6 hours. The reaction mixture was diluted with ice then poured into water (1000 ml), then filtered. The solid was dried then subjected to flash chromatography on silica eluting with a mixture of toluene and dichloromethane (2:1, v/v) to give the title compound as a white solid, m.p. 185-187° C.

Workup

  1. waitstanding at room temperature for 18 hours
  2. stirringthen stirred for 6 hours
  3. additionThe reaction mixture was diluted with ice
  4. filtrationfiltered
  5. customThe solid was dried
  6. additionthen subjected to flash chromatography on silica eluting with a mixture of toluene and dichloromethane (2:1

Sources & evidence

ORD record
ord-bb2dfa62c5934166b5bbce512b8a9383
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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