Methanol → Methyl 5-hydroxy-2-methyl-3-nitrobenzoate

HRID 2208945Notes

Reaction equation

HRID 2208945 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 23009717HCID 23009717, compound

Product 1

HCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoateYield 80%

Procedure

To a stirred solution of 5-hydroxy-2-methyl-3-nitrobenzoic acid (3.50 g, 17.8 mmol) in methanol (40 mL), was added thionyl chloride (3.9 mL, 53 mmol) at 0° C. The mixture was heated under reflux for 3 hours and concentrated under reduced pressure. Aqueous sodium bicarbonate was added to the residue which was extracted with ethyl acetate. The combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (3.0 g, 80%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. additionAqueous sodium bicarbonate was added to the residue which
  5. extractionwas extracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-baa371fb034a493ab338803bba5e0607
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

Loading…