4-Nitrophenol → HCID 459027, compound

HRID 1577856Notes

Reaction equation

HRID 1577856 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:11]([OH:14])([CH3:13])[CH3:12].[CH2:15]([CH:17]1[O:19][CH2:18]1)Cl.[OH-:20].[K+]>O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:15][CH:17]([OH:19])[CH2:18][O:14][C:11]2[CH:13]=[CH:9][C:4]([N+:1]([O-:2])=[O:20])=[CH:5][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 3776Isopropanol2×HCID 7835EpichlorohydrinHCID 14797Potassium Hydroxide

Product 1

HCID 459027HCID 459027, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.86 g. (63.7 mmol) of 4-nitrophenol is dissolved in 250 ml. of isopropanol; 2.75 ml. (35.1 mmol) of epichlorohydrin is added thereto, and thereafter a solution of 1.98 g. (35.3 mmol) of potassium hydroxide in 25 ml. of isopropanol as well as 1 ml. of water are introduced. The mixture is refluxed for 48 hours, concentrated to half its volume, and combined with 50 ml of water. The thus-precipitated product is filtered off and recrystallized from isopropanol/ethanol 1:1. Melting point: 144°-145° C. Yield: 6.4 g.

Workup

  1. temperatureThe mixture is refluxed for 48 hours
  2. concentrationconcentrated to half its volume
  3. filtrationThe thus-precipitated product is filtered off
  4. customrecrystallized from isopropanol/ethanol 1:1

Sources & evidence

ORD record
ord-2d293bc2372048e9a397920a879e47dc
Source dataset
uspto-grants-1981_09
Patent number
US04289777

Reaction notes

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