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

HRID 638728

Reaction equation

HRID 638728 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) and heated to reflux for 48 hours. Acetone was distilled off and water (2 L) was added. Crude 39 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 39 (130 g, 45.1%) as a white powder. M.p: 84.5.5-86.6° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. distillationAcetone was distilled off
  4. additionwater (2 L) was added
  5. filtrationCrude 39 was filtered
  6. customdried
  7. customrecrystallised from a mixture of ethyl acetate:hexane (1:6)

Sources & evidence

ORD record
ord-6c566cbc9ab746a8a9126547a6df3a8e
Source dataset
uspto-grants-2010_04
Patent number
US07691364B2

Linked notes

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