4-Nitrophenol → HCID 459027, compound

HRID 1379353Notes

Reaction equation

HRID 1379353 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.[OH-:16].[Na+]>CN(C)C=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:8][CH:7]([OH:10])[CH2:14][O:15][C:13]2[CH:11]=[CH:9][C:4]([N+:1]([O-:2])=[O:16])=[CH:5][CH:6]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide

Product 1

HCID 459027HCID 459027, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1 g (7.2 mmol) of 4-nitrophenol, 0.28 ml (3.6 mmol) of epichlorohydrin, and 0.16 g (3.96 mmol) of sodium hydroxide in 2 ml of dimethylformamide was heated at 110° C. for 1 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography using chloroform to give 0.97 g (81%) of the desired compound (Rf 0.42, 40% ethyl acetate in chloroform). 1H NMR (CDCl3) δ 2.54 (d, 5 Hz, 1H), 4.28 (dd, J=10, 6 Hz, 2H), 4.29 (dd, J=10, 5 Hz, 2H), 4.50 (br sextet, J=6 Hz, 1H), 7.0-7.05 (m, 4H), 8.2-8.3 (m, 4H). Mass spectrum (M+NH4)+ =352.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-31939db3d3a84889adffa1bdcb8a1b10
Source dataset
uspto-grants-1997_09
Patent number
US05670675

Reaction notes

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