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

HRID 1398248Notes

Reaction equation

HRID 1398248 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), Potassium carbonate (600 g), sodium iodide (10 g) in anhydrous acetone (2.1 liter) was added methyl 6-bromohexanoate (156 g) and heated to reflux for 48 hours. Acetone was distilled and water (2 liter) was added. Crude 6-(4-nitrophenoxy)-hexanoic acid methyl ester was filtered, dried and recrystallised from a mixture of ethyl acetate and hexane (1:6) to obtain pure 6-(4-nitrophenoxy)-hexanoic acid methyl ester (130 g) as a white powder with a melting point of 84.5.5-86.6° C. The product was characterized by 1H NMR (CDCl3) δ 1.56 (m, 2H, CH2), 1.74 (m, 2H, CH2), 1.90 (s, 2H, CH2), 3.68 (s, 3H, Ester), 4.06 (t, 2H, CH2), 6.92 (d, 2H, Ar), 8.20 (d, 2H, Ar).

Workup

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. distillationAcetone was distilled
  4. additionwater (2 liter) was added
  5. filtrationCrude 6-(4-nitrophenoxy)-hexanoic acid methyl ester was filtered
  6. customdried
  7. customrecrystallised from a mixture of ethyl acetate and hexane (1:6)

Sources & evidence

ORD record
ord-3b64d7164b64497aa1833a009e345f7f
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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