Ethanol → Ethyl 2-methyl-5-nitrobenzoate

HRID 1370567Notes

Reaction equation

HRID 1370567 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH2:19](O)[CH3:20]>>[CH3:6][C:7]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:8]=1[C:9]([O:11][CH2:19][CH3:20])=[O:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 18510875Ethyl 2-methyl-5-nitrobenzoate

Procedure

Concentrated sulfuric acid (12 ml) was added to a solution of 2-methyl-5-nitrobenzoic acid (10.87 g) in ethanol (60 ml). The mixture was heated under reflux overnight. The reaction solution was concentrated under the reduced pressure. Water was then added to the residue. The mixture was extracted with diethyl ether. The extract was washed with water and saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give ethyl 2-methyl-5-nitrobenzoate (11.86 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction solution was concentrated under the reduced pressure
  4. additionWater was then added to the residue
  5. extractionThe mixture was extracted with diethyl ether
  6. washThe extract was washed with water and saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was then removed by distillation under the reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3f8a333366414e879f155bc707f4cc90
Source dataset
uspto-grants-2003_06
Patent number
US06583144B2

Reaction notes

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