4-Nitrophenol → HCID 117716329, compound

HRID 1398256Notes

Reaction equation

HRID 1398256 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(N(CC)CC)C.[N+:18]([C:21]1[CH:32]=[CH:31][C:24]([O:25][CH:26]([CH3:30])[C:27](Cl)=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:27](=[O:28])[CH:26]([O:25][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:32][CH:31]=2)[CH3:30])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 15315733HCID 15315733, compound

Product 1

HCID 117716329HCID 117716329, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-nitrophenol (21.8 g) and triethylamine (33 ml) in ethyl acetate (360 ml) at 0° C. was added 2-(4-nitrophenoxy)-propionyl chloride (36 g) dropwise, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was filtered to remove the salts, washed with 5% sodium bicarbonate, followed by water, and the ethyl acetate layer was dried over anhydrous sodium sulphate. The solvent was distilled off under vacuum and the compound was precipitated by adding cold methanol. Filtration and drying gave pure 2-(4-nitrophenoxy)-propionic acid-4-nitrophenyl ester (35 g) as white powder. The product had a melting point of 136-139° C., with a purity of 99%. The product was characterized by 1H NMR (CDCl3) δ 1.85 (d, 3H, CH3), 5.15 (q, 1H, CH), 7.05 (d, 2H, Ar), 7.28 (d, 2H, Ar), 8.30 (m, 4H, Ar).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the salts
  3. washwashed with 5% sodium bicarbonate
  4. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulphate
  5. distillationThe solvent was distilled off under vacuum
  6. customthe compound was precipitated
  7. additionby adding cold methanol
  8. filtrationFiltration
  9. customdrying

Sources & evidence

ORD record
ord-d134fcdaab994f6abb902da256862459
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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