4-Nitrophenol → HCID 117716281, compound

HRID 1398259Notes

Reaction equation

HRID 1398259 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[CH2:27][C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][C:37](=[O:40])[CH2:38]Cl)=[O:29]>CC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:27][C:28]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][C:37](=[O:40])[CH2:38][O:14][C:11]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[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 15376062Oxydi(ethane-2,1-diyl) bis(chloroacetate)

Product 1

HCID 117716281HCID 117716281, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-nitrophenol (966 g), potassium carbonate (4.26 Kg), sodium iodide (60 g), and disodium phosphate (60 g) in acetone (10 L) was added chloro-acetic acid 2-[2-(2-chloro-acetoxy)-ethoxy]-ethyl ester (1 Kg) and the mixture was stirred at reflux for 8 hours. Acetone was distilled off and cold water (250 ml) was added. The crude product was filtered off and slurried in methanol (10 L), re-filtered and dried to give (4-nitrophenoxy)-acetic acid 2-{2-[2-(4-nitrophenoxy)-acetoxy]-ethoxy}-ethyl ester (1450 grams) as a white powder with a melting point of 73-75° C. The product was characterized by 1H NMR (CDCl3) δ 3.62 (t, 2H, CH2), 4.40 (t, 2H, CH2), 4.78 (s, 2H, CH2), 6.95 (d, 2H, Ar), 8.15 (d, 2H, Ar).

Workup

  1. temperatureat reflux for 8 hours
  2. distillationAcetone was distilled off
  3. additioncold water (250 ml) was added
  4. filtrationThe crude product was filtered off
  5. filtrationre-filtered
  6. customdried

Sources & evidence

ORD record
ord-6e0aa5f8ad194f16b0f1fc45f375fc9e
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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