Methanol → Methyl (4-nitrophenoxy)acetate

HRID 1458688Notes

Reaction equation

HRID 1458688 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH3:19]O>>[N+:5]([C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([O:16][CH3:19])=[O:15])=[CH:17][CH:18]=1)([O-:7])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 15720(4-Nitrophenoxy)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 700522Methyl (4-nitrophenoxy)acetateYield 96%

Procedure

Thionyl chloride (2.3 ml) was added dropwise under ice cooling to a solution of 5.0 g (25 mmol) of 4-nitrophenoxyacetic acid in 250 ml of methanol, followed by stirring at room temperature for 1 hour. After the solvent was distilled out under reduced pressure, the residue was dissolved in 50 ml of methylene chloride, followed by neutralization with an aqueous solution of sodium hydrogencarbonate. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over sodium sulfate. The solvent was thereafter distilled out under reduced pressure, whereby 5.2 g of pale yellow powder were obtained (yield: 96%).

Workup

  1. distillationAfter the solvent was distilled out under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml of methylene chloride
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was thereafter distilled out under reduced pressure

Sources & evidence

ORD record
ord-4e724a22bfb740b7b65152d930c9694d
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

Loading…