Methanol → Methyl p-nitrophenylacetate

HRID 1668809Notes

Reaction equation

HRID 1668809 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH3:19]O>>[CH3:19][O:17][C:16](=[O:18])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 4661(4-Nitrophenyl)acetic acid

Product 1

HCID 270191Methyl p-nitrophenylacetate

Procedure

Concentrated sulfuric acid (1 mL) was added to a solution of 4-nitrophenylacetic acid (10.0 g, 55.2 mmol) in anhydrous MeOH and heated under reflux for 3 hours. After evaporation of solvent under reduced pressure the mixture was dissolved in ethyl acetate and washed sequentially with 5% sodium bicarbonate, water, and brine. The organic phase was dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was solidified on standing at a temperature in the range of 15° C. to 40° C. to afford the title compound as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. customAfter evaporation of solvent under reduced pressure the mixture
  4. dissolutionwas dissolved in ethyl acetate
  5. washwashed sequentially with 5% sodium bicarbonate, water, and brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customon standing at a temperature in the range of 15° C. to 40° C.

Sources & evidence

ORD record
ord-99903a3aad6444f589543046264430c6
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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