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

HRID 2208919Notes

Reaction equation

HRID 2208919 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 reaction mixture was heated at reflux for 3 h. On completion, the solvent was removed under reduced pressure. Aqueous sodium bicarbonate was added, followed by extraction 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 reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. customOn completion, the solvent was removed under reduced pressure
  4. additionAqueous sodium bicarbonate was added
  5. extractionfollowed by extraction 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-5bbb6da1ef2944d6b56a8a93ac378f12
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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