Methanol → Methyl 5-nitrosalicylate

HRID 1085272Notes

Reaction equation

HRID 1085272 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH3:19]O>>[N+:6]([C:9]1[CH:17]=[C:13]([C:14]([O:16][CH3:19])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=1)([O-:8])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73185-Nitrosalicylic acid

Product 1

HCID 87041Methyl 5-nitrosalicylate

Procedure

80 ml of methanol and 10 g of concentrated sulfuric acid were added to 5 g of 5-nitrosalicylic acid. The resultant mixture was heated under stirring for 8 hours while distilling methanol off. The solvent was then distilled off under reduced pressure and the residue was dissolved in chloroform. The resultant chloroform solution was washed with water and then concentrated to dryness. The resultant residue was purified by chromatography on a silica gel column (eluent: chloroform), followed by recrystallization from chloroform-ether to obtain 5.1 g of methyl 5-nitrosalicylate as crystals.

Workup

  1. distillationwhile distilling methanol off
  2. distillationThe solvent was then distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe resultant chloroform solution was washed with water
  5. concentrationconcentrated to dryness
  6. customThe resultant residue was purified by chromatography on a silica gel column (eluent: chloroform)
  7. customfollowed by recrystallization from chloroform-ether

Sources & evidence

ORD record
ord-1e1611e2e7b34363b54b8eda74281a88
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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