4-Nitrophenol → HCID 117716267, compound

HRID 1398263Notes

Reaction equation

HRID 1398263 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-].[Na+].P(O)([O-])([O-])=O.[Na+].[Na+].Cl[CH:27]([CH3:42])[C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][C:37](=[O:41])[CH:38](Cl)[CH3:39])=[O:29]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:27]([CH3:42])[C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][C:37](=[O:41])[CH:38]([O:14][C:11]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH3:39])=[O:29])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 24203Sodium Phosphate, DibasicHCID 346305Propanoic acid, 2-chloro-, oxydi-2,1-ethanediyl ester

Product 1

HCID 117716267HCID 117716267, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-nitrophenol (2.6 Kg), potassium carbonate (11.5 Kg), sodium iodide (100 g), and disodium phosphate (100 g) in acetone (30 L) was added 2-chloropropionic acid 2-[2-(2-chloro-propionyloxy)-ethoxy]-ethyl ester (3 Kg). The reaction mixture was refluxed with stirring for 48 hours. The acetone was distilled off and cold water (25 L) was added. The crude product was extracted into chloroform (15 L) and the chloroform extract was dried over anhydrous sodium sulphate. Chloroform was distilled off and the final product was precipitated from methanol. The solid was collected by filtration, dried and recrystallised to give (4-nitrophenoxy)-propionic acid 2-{2-[2-(4-nitrophenoxy)-propionyloxy]-ethoxy}-ethyl ester (745 grams) as a white powder. The product was characterized by 1H NMR (CDCl3) δ 1.65 (d, 3H, CH3), 3.65 (t, 2H, CH2), 4.30 (t, 2H, CH2), 4.85 (q, 1H, CH), 6.90 (d, 2H, Ar), 8.20 (d, 2H, Ar).

Workup

  1. temperatureThe reaction mixture was refluxed
  2. distillationThe acetone was distilled off
  3. additioncold water (25 L) was added
  4. extractionThe crude product was extracted into chloroform (15 L)
  5. extractionthe chloroform extract
  6. dry with materialwas dried over anhydrous sodium sulphate
  7. distillationChloroform was distilled off
  8. customthe final product was precipitated from methanol
  9. filtrationThe solid was collected by filtration
  10. customdried
  11. customrecrystallised

Sources & evidence

ORD record
ord-4e2e14d65cdd4b36811799dcda6bb87b
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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