Ethanol → Ethyl 4-nitrophenylacetate

HRID 394938Notes

Reaction equation

HRID 394938 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]>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH2:21][CH3:22])=[O:12])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

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

Product 1

HCID 79517Ethyl 4-nitrophenylacetate

Procedure

10 g of 4-nitrophenylacetic acid dissolved in 100 ml of ethanol were treated with 3 ml of concentrated sulfuric acid. The mixture was heated to reflux for 18 hours. After cooling to room temperature, the mixture was neutralized with 2 N sodium hydroxide solution then was extracted with two portions of 200 ml ethyl acetate. The combined extracts were washed with one portion of 100 ml of saturated aqueous sodium chloride solution then dried over MgSO4 and concentrated in vacuo, yielding 11.5 g of a white solid that was used without purification. 1H NMR (CDCl3): 8.19 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 4.18 (q, J=7.1 Hz, 2H), 3.73 (s, 2H), 1.27 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. extractionthen was extracted with two portions of 200 ml ethyl acetate
  4. washThe combined extracts were washed with one portion of 100 ml of saturated aqueous sodium chloride solution
  5. dry with materialthen dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7960ca1754948ffbe0e8c27da47135a
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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