Methanol → Methyl 2-(2-nitrophenyl)acetate

HRID 1381508Notes

Reaction equation

HRID 1381508 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.[OH-].[NH4+].[CH3:21]O>>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([O:13][CH3:21])=[O:12])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 520464Methyl 2-(2-nitrophenyl)acetate

Procedure

To a solution of 2-nitrophenylacetic acid (2.00 kg) in methanol (4 l) at room temperature is added concentrated sulfuric acid (71.0 ml) all at once. The solution is stirred and refluxed for 6 hours, then allowed to stand at room temperature overnight. After cooling in an ice bath to 7°, the solution is adjusted to pH 8 by the addition of concentrated ammonium hydroxide (150 ml), keeping the temperature below 10°. The solution is concentrated in vacuo to a volume of 2 l and is then admixed with dichloromethane (2.5 l). The combined solution is washed with water (2×500 ml) and brine (500 ml), dried over anhydrous magnesium sulfate, and evaporated to yield crude product which is distilled to give methyl 2-nitrophenylacetate, b.p. 116°-131° (0.2 mm Hg).

Workup

  1. temperaturerefluxed for 6 hours
  2. temperatureAfter cooling in an ice bath to 7°
  3. customthe temperature below 10°
  4. concentrationThe solution is concentrated in vacuo to a volume of 2 l
  5. washThe combined solution is washed with water (2×500 ml) and brine (500 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated
  8. customto yield crude product which
  9. distillationis distilled

Sources & evidence

ORD record
ord-522c87d556de40a39972d283abf7aa07
Source dataset
uspto-grants-1989_02
Patent number
US04803197

Reaction notes

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