4-Nitrophenol → HCID 117716265, compound

HRID 1398267Notes

Reaction equation

HRID 1398267 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:11](=[O:14])([O-])[O-].[K+].[K+].[I-].[K+].P(O)([O-])([O-])=O.[Na+].[Na+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][C:41](=[O:48])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]Br)=[O:33]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][C:41](=[O:48])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][O:14][C:11]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[O:33])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 9804-NitrophenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 117716545HCID 117716545, compound

Product 1

HCID 117716265HCID 117716265, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into a mixture of 4-nitrophenol (60.5 g), potassium carbonate (180 g), potassium iodide (15 g), and disodium phosphate (15 g) in acetone (1000 ml) was added 6-bromohexanoic acid 2-[2-(6-bromohexanoyloxy)-ethoxy]-ethyl ester (100 g). The solution was stirred at reflux for 24 hours. The acetone layer was distilled off and cold water (250 ml) was added. The crude product was extracted into chloroform and the chloroform extract was washed with 5% sodium bicarbonate solution (800 ml) followed by water (600 ml). The chloroform layer was dried over anhydrous sodium sulphate and distilled, and the final product was precipitated by adding diisopropyl ether. The crude product was isolated by filtration and drying. The final product was recrystallized using a mixture of ethyl acetate and diisopropyl ether (1:3) to give pure 6-(4-nitrophenoxy)-hexanoic acid 2-{2-[6-(4-nitrophenoxy)-hexanoyloxy]-ethoxy}-ethyl ester (100 grams) as a white powder. The product was characterized by 1H NMR (CDCl3) δ 1.50 (m, 2H, CH2), 1.70 (m, 2H, CH2), 1.82 (m, 2H, CH2), 2.38 (t, 2H, CH2), 3.74 (t, 2H, CH2), 4.08 (t, 2H, CH2), 4.26 (t, 2H, CH2), 6.92 (d, 2H, Ar), 8.20 (d, 2H, Ar). The product has a melting point of 60-62° C.

Workup

  1. temperatureat reflux for 24 hours
  2. distillationThe acetone layer was distilled off
  3. additioncold water (250 ml) was added
  4. extractionThe crude product was extracted into chloroform
  5. extractionthe chloroform extract
  6. washwas washed with 5% sodium bicarbonate solution (800 ml)
  7. dry with materialThe chloroform layer was dried over anhydrous sodium sulphate
  8. distillationdistilled
  9. customthe final product was precipitated
  10. additionby adding diisopropyl ether
  11. customThe crude product was isolated by filtration
  12. customdrying
  13. customThe final product was recrystallized
  14. additiona mixture of ethyl acetate and diisopropyl ether (1:3)

Sources & evidence

ORD record
ord-12730920900a42c8904b4e56d88607b2
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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