Methanol → Methyl 4-chloro-3-methylsulfonyl-5-nitrobenzoate

HRID 399789Notes

Reaction equation

HRID 399789 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].S(=O)(=O)(O)O.[CH3:23]O>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([O:8][CH3:23])=[O:7])=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 122745753-Methylsulfonyl-4-chloro-5-nitrobenzoic acid

Product 1

HCID 18945451Methyl 4-chloro-3-methylsulfonyl-5-nitrobenzoate

Procedure

The mixture of 4-chloro-3-methylsulfonyl-5-nitrobenzoic acid (10.0 g) and conc. sulfuric acid (5.0 ml) in methanol (100.0 ml) was heated under reflux for 10 hours and the mixture was evaporated in vacuo. To the residue was added water and the mixture was adjusted to pH 8 with potassium carbonate. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give methyl 4-chloro-3-methylsulfonyl-5-nitrobenzoate (10.23 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. customthe mixture was evaporated in vacuo
  4. additionTo the residue was added water
  5. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  6. washThe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-ef854fd20c184e93ba7d71facb6dcd5f
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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