Methanol → Salicylic acid, 4-nitro-, methyl ester

HRID 280832Notes

Reaction equation

HRID 280832 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]O>S(=O)(=O)(O)O>[OH:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

4

Reactant 2

HCID 887MethanolHCID 692664-Nitrosalicylic acid

Product 1

HCID 139539Salicylic acid, 4-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-hydroxy-4-nitrobenzoic acid (25 g) was dissolved in 100 ml of methanol and sulfuric acid (11 ml, density 1.84). The solution was boiled for 24 hrs, whereupon it was poured onto ice water and extracted with chloroform. The chloroform phase was shaken against sodium hydrogen carbonate solution, dried with magnesium sulfate and evaporated. The product was crystallized from methanol. Yield: 21 g.

Workup

  1. additionwas poured onto ice water
  2. extractionextracted with chloroform
  3. dry with materialdried with magnesium sulfate
  4. customevaporated
  5. customThe product was crystallized from methanol

Sources & evidence

ORD record
ord-5703b5d6de4b4f1faa1fd8a3a014c4fe
Source dataset
uspto-grants-1986_05
Patent number
US04591584

Reaction notes

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