4-Nitrophenol → HCID 117716334, compound

HRID 1398251Notes

Reaction equation

HRID 1398251 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:35]=[CH:34][C:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32])=[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:31](=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:35][CH:34]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 117716382HCID 117716382, compound

Product 1

HCID 117716334HCID 117716334, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-nitrophenol (10.8 g), triethylamine (22 ml) in ethyl acetate (200 ml) at 0° C. was added 6-(4-nitrophenoxy)-hexanoyl chloride (20 g) dropwise, and the mixture was further stirred at room temperature for 16 hours. The reaction mixture was filtered to remove the salts, washed with 5% sodium bicarbonate, water and dried over anhydrous sodium sulphate. The solvent was distilled off under vacuum and the pure compound was precipitated by adding cold methanol. After filtration and drying, the compound was further recrystallized from a mixture of chloroform and methanol (1:1) to give pure 6-(4-nitrophenoxy)-hexanoic acid 4-nitrophenyl ester (15 grams) as white powder with a melting point of 73-76° C. The product was also characterized by 1H NMR (CDCl3) δ 1.60 (m, 2H, CH2), 1.85 (m, 6H, CH2X2), 2.70 (t, 2H, CH2), 4.10 (t, 2H, CH2), 6.95 (d, 2H, Ar), 7.30 (d, 2H, Ar), 8.25 (m, 4H, Ar).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the salts
  3. washwashed with 5% sodium bicarbonate, water
  4. dry with materialdried over anhydrous sodium sulphate
  5. distillationThe solvent was distilled off under vacuum
  6. customthe pure compound was precipitated
  7. additionby adding cold methanol
  8. filtrationAfter filtration
  9. customdrying
  10. customthe compound was further recrystallized from a mixture of chloroform and methanol (1:1)

Sources & evidence

ORD record
ord-d384df5635c9426e91f1ff9089a21d5d
Source dataset
uspto-grants-2014_12
Patent number
US08901347B1

Reaction notes

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