Ethyl Acetate → Methyl 2-(2-nitrophenyl)acetate

HRID 2200161Notes

Reaction equation

HRID 2200161 reaction equation
S(Cl)(Cl)(=O)=O.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17])([O-:8])=[O:7].[CH3:19]COC(C)=O>CO>[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24648Sulfuryl chlorideHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 520464Methyl 2-(2-nitrophenyl)acetateYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sulfonyl chloride (3 mL) dropwise to a solution of 2-nitrophenylacetic acid (7.0 g, 38.6 mmol) in methanol (20 mL) at 0° C., reflux the resulting mixture overnight. TLC (PE:EtOAc=3:1) shows the reaction is complete. Concentrate the reaction mixture under reduced pressure, add water, extract with ethyl acetate twice, and wash the combined organic layers with brine, dry over anhydrous sodium sulfate. Concentrate under reduced pressure to yield the crude product (7.5 g, 94.7%) which is used directly without further purification. MS: (M+1): 196.1.

Workup

  1. temperaturereflux the resulting mixture overnight
  2. concentrationConcentrate the reaction mixture under reduced pressure
  3. additionadd water
  4. extractionextract with ethyl acetate twice
  5. washwash the combined organic layers with brine
  6. dry with materialdry over anhydrous sodium sulfate
  7. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-8c1a23792a4f4c1eb12318609933a5ea
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

Loading…