Methanol → Methyl 2-(2-nitrophenyl)acetate

HRID 1276314Notes

Reaction equation

HRID 1276314 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:19]O>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:19])=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 520464Methyl 2-(2-nitrophenyl)acetate

Procedure

A mixture of 2-nitrophenylacetic acid (300 g, 1.66 mol) and sulfuric acid (d=1.84 g/ml, 6 ml) in methanol (61) was heated under reflux for 21 h. The solvent was removed in vacuo and the residue dissolved in dichloromethane (21). The dichloromethane solution was then washed with saturated aqueous sodium carbonate solution (600 ml), brine (500 ml), dried (MgSO4), filtered and then evaporated in vacuo.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 21 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane (21)
  5. washThe dichloromethane solution was then washed with saturated aqueous sodium carbonate solution (600 ml), brine (500 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-7d1498df638340f78bb02cf4df4fde76
Source dataset
uspto-grants-2000_12
Patent number
US06166040

Reaction notes

Loading…