Ethanol → Ethyl 4-nitrophenylacetate

HRID 82287Notes

Reaction equation

HRID 82287 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].S(=O)(=O)(O)O.[OH-].[Na+].[CH2:21](O)[CH3:22]>>[CH2:21]([O:12][C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH3:22]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 4661(4-Nitrophenyl)acetic acidHCID 14798Sodium Hydroxide

Product 1

HCID 79517Ethyl 4-nitrophenylacetateYield 98%

Procedure

To a stirred solution of (4-nitro-phenyl)-acetic acid (3 g, 16.4 mmol) in ethanol (30 mL) was added sulphuric acid (1 mL) and the reaction mixture was heated to reflux for 16 hours. The reaction mixture was neutralized with 2N aq. NaOH solution and extracted with EtOAc (3×50 mL). The combined organic layers were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a light yellow oil in 98% yield, 3.4 g.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b9f9ab498404a8ab71a0ea8bcffc870
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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