Methanol → Methyl p-nitrophenylacetate

HRID 1842975Notes

Reaction equation

HRID 1842975 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:14]O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 4661(4-Nitrophenyl)acetic acid

Product 1

HCID 270191Methyl p-nitrophenylacetateYield 98%

Procedure

To a stirred MeOH (100 mL) solution of 2-(4-nitrophenyl)acetic acid (10.0 g, 55.202 mmol, 1.0 eq) SOCl2 (6.7 mL, 110.045 mmol, 2.0 eq) was added at 0° C. for 10 min and the mixture was stirred at RT for 2 h, then excess of SOCl2 was removed under vacuum and the residue was dissolved in EtOAC (50 mL), washed with water, sat. (aq) NaHCO3, dried (Na2SO4) and the solvent was evaporated to get methyl 2-(4-nitrophenyl)acetate (10.5 g, 98%, solid; TLC system: EtOAc/PE (3:7), Rf: 0.60).

Workup

  1. customexcess of SOCl2 was removed under vacuum
  2. dissolutionthe residue was dissolved in EtOAC (50 mL)
  3. washwashed with water, sat. (aq) NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-44d2ee0eeb4245cca41e1e2ca70f217a
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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