Water → HCID 17815456, compound

HRID 1373233Notes

Reaction equation

HRID 1373233 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18]C)=[O:17])=[CH:11][CH:10]=1)([O-:5])=[O:4].O.S([O-])(O)(=O)=O.[K+]>O1CCCC1.CO>[N+:3]([C:6]1[CH:23]=[CH:22][CH:21]=[CH:20][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:13][CH:14]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 12789607HCID 12789607, compound

Product 1

HCID 17815456HCID 17815456, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Aqueous 1 N sodium hydroxide solution (41.7 ml, 41.7 mmols) was added to a solution of methyl 4-(2-nitrophenoxy)phenylacetate (2.7 g, 9.3 mmols) in tetrahydrofuran (50 ml) and methanol (50 ml). The resulting mixture was stirred at 40° C. for 1 hour. Water and potassium hydrogensulfate (5.68 g, 41.7 mmols) were added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting solid was recrystallized from ethyl acetate/hexane to give a crystal of 4-(2-nitrophenoxy)phenylacetic acid (1.83 g, 71.8%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationThis was concentrated under reduced pressure
  5. customthe resulting solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-efe0f2e02dc7493b9c9199f2c6abd1a4
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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