Methanol → HCID 60451708, compound

HRID 417303Notes

Reaction equation

HRID 417303 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:9]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].OS(O)(=O)=O.[CH3:23]O>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16])[C:9]([O:11][CH3:23])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2535313-Butoxy-4-nitrobenzoic acid

Product 1

HCID 60451708HCID 60451708, compoundYield 95%

Procedure

To a solution of 3-butoxy-4-nitrobenzoic acid (City Chemicals) (2.5 g, 10.5 mmol) in methanol (10 mL) were added concentrated H2SO4 (1 g, 10.5 mmol). The reaction mixture was heated at reluxing for 2 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate twice. The combined organic extract was washed with water, aqueous saturated NaHCO3 solution, brine, dried over MgSO4, and concentrated to give methyl 3-butoxy-4-nitrobenzoate as a brown oil (2.5 g, 95%).

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe mixture was concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionaqueous layer was extracted with ethyl acetate twice
  6. extractionThe combined organic extract
  7. washwas washed with water, aqueous saturated NaHCO3 solution, brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3aeefc76e4004d3997b01eafcac4050b
Source dataset
uspto-grants-2012_01
Patent number
US08088815B2

Reaction notes

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