Phenol → Ethyl 4-(2-nitrophenoxy)butanoate

HRID 1003238Notes

Reaction equation

HRID 1003238 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].Br[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].C1(O)C=CC=CC=1>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 996PhenolHCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12433959Ethyl 4-(2-nitrophenoxy)butanoateYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-nitrophenol (1) (1.4 g, 10 mM) and ethyl 4-bromobutyrate (2.1 g, 1.57 mL, 11 mM) in 35 mL of dry acetone is added 2 g (14.5 mM) of anhydrous, ground potassium carbonate. The resultant colored mixture is then heated under a nitrogen atmosphere at gentle reflux until the color due to the phenol anion has dissipated and a yellow mixture remains. Concentration of the cooled and filtered mixture yields an oil which on flash chromatography (silica gel, ethyl acetate/hexane- or methylene chloride as eluant) yields 2.4 g (96% yield) of the title compound (3) as an oily liquid.

Workup

  1. temperatureThe resultant colored mixture is then heated under a nitrogen atmosphere
  2. temperatureConcentration of the cooled
  3. filtrationfiltered mixture
  4. customyields an oil which on flash chromatography (silica gel, ethyl acetate/hexane- or methylene chloride as eluant)

Sources & evidence

ORD record
ord-9cf956e0d57a49ea94834b9aab91106b
Source dataset
uspto-grants-2000_04
Patent number
US06046183

Reaction notes

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