4-Nitrophenol → 6-(4-Nitrophenoxy)-hexanoic acid methyl ester

HRID 501842

Reaction equation

HRID 501842 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC(C)=O>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl esterYield 65.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-nitrophenol (150 g, 1.079 moles), potassium carbonate (600 g, 4.341 moles) and sodium iodide (10 g, 66.7 mmol) in anhydrous acetone (2.1 L) was added methyl 6-bromohexanoate (156 g, 746.41 mmol) with and heating to reflux for 48 hours. Acetone was distilled off and water (2 L) was added. Crude 21 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 21 (130 g, 45.1%) as a white powder with an m.p. between 84.5.5-86.6° C.

Workup

  1. temperatureheating
  2. temperatureto reflux for 48 hours
  3. distillationAcetone was distilled off
  4. additionwater (2 L) was added
  5. filtrationCrude 21 was filtered
  6. customdried
  7. customrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Sources & evidence

ORD record
ord-870c51f8df9d4d22876604cf77809c32
Source dataset
uspto-grants-2010_08
Patent number
US07772352B2

Linked notes

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