Ethanol → Ethyl 2-nitro-5-phenoxybenzoate

HRID 2099972Notes

Reaction equation

HRID 2099972 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].OS(O)(=O)=O.C([O-])(O)=O.[Na+].[CH3:30][CH2:31]O>>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][C:5]=1[C:6]([O:8][CH2:30][CH3:31])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 142334252-Nitro-5-phenoxybenzoic acid

Product 1

HCID 57796884Ethyl 2-nitro-5-phenoxybenzoateYield 65%

Procedure

A solution of 34A (4.5 g, 17.4 mmol) in EtOH (120 mL) was treated with concentrated H2SO4 (4 mL) and heated to reflux for 24 hours. The mixture was cooled to room temperature and neutralized with 5% NaHCO3. The resulting solution was extracted with CH2Cl2, dried (MgSO4), filtered, and concentrated to afford 43A (2.6 g, 65%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. extractionThe resulting solution was extracted with CH2Cl2
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c9f970aa0c594391b9456f0417f654a3
Source dataset
uspto-grants-2009_08
Patent number
US07569725B2

Reaction notes

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