Methanol → Methyl 3-hydroxy-2-nitrobenzoate

HRID 1017594Notes

Reaction equation

HRID 1017594 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[C:7]([N+:15]([O-:17])=[O:16])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([OH:11])=[O:10].[CH3:18]O>>[OH:5][C:6]1[C:7]([N+:15]([O-:17])=[O:16])=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([O:11][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2932913-Hydroxy-2-nitrobenzoic acid

Product 1

HCID 13659833Methyl 3-hydroxy-2-nitrobenzoate

Procedure

To a methanol solution (15 mL) at 0° C. was dropwise added thionyl chloride (6.4 mL, 0.088 mol). After 15 minutes, 3-hydroxy-2-nitrobenzoic acid (4 g, 0.022 mol) was added and the resulting mixture was stirred at room temperature for 72 hours. Volatile was removed under vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and saturated sodium chloride, and was dried over sodium sulfate. After concentration, the crude product was recrystallized from dichloromethane and hexane to gave 4.5 g of methyl 3-hydroxy-2-nitrobenzoate.

Workup

  1. customat 0° C.
  2. customVolatile was removed under vacuo
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and saturated sodium chloride
  6. dry with materialwas dried over sodium sulfate
  7. concentrationAfter concentration
  8. customthe crude product was recrystallized from dichloromethane and hexane

Sources & evidence

ORD record
ord-e12950f9e96b43dbb5a7d1008d0a06ff
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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