Water → Ethyl 3-[4-(4-nitrophenoxy)phenyl]propionate

HRID 884084Notes

Reaction equation

HRID 884084 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[N+:22]([C:19]1[CH:20]=[CH:21][C:16]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)=[CH:17][CH:18]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 2736435Ethyl 4-hydroxyhydrocinnamate

Product 1

HCID 68524232Ethyl 3-[4-(4-nitrophenoxy)phenyl]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 3-(4-hydroxyphenyl)-propionate (6.00 g, 30.9 mmol) in DMF (60 mL) were added 4-fluoronitrobenzene (6.54 g, 46.3 mmol) and potassium carbonate (5.12 g, 37.1 mmol). The resulting reaction solution was stirred for 1 hour at 80° C. To the reaction solution was added water and extracted with ethyl acetate. The resulting ethyl acetate layer was washed with water and then with brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 9.64 g of the title compound.

Workup

  1. customThe resulting reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe resulting ethyl acetate layer was washed with water
  4. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-7f7c40b2c53d4caea4915e6b000d667f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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