4-Nitrophenol → 1,1'-Oxybis(4-nitrobenzene)

HRID 1595151Notes

Reaction equation

HRID 1595151 reaction equation
[OH-:1].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4]>>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:9]2[CH:10]=[CH:11][C:6]([N+:3]([O-:4])=[O:1])=[CH:7][CH:8]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

3

Reactant 2

HCID 9804-NitrophenolHCID 14797Potassium Hydroxide

Product 1

HCID 75681,1'-Oxybis(4-nitrobenzene)

Procedure

From N-Boc-D-cHyp(Tosyloxy)-OMe (5.27 mmol, 2.50 g), powdered KOH (13.2 mmol, 0.74 g), and 4-nitrophenol (13.2 mmol, 1.83 g), held at reflux for 6 days, the 4-nitrophenyl ether of D-trans-hydroxyproline methyl ester (0.39 g, 20%, m.p. 154-155° C.) was obtained after purification by column chromatography (silica gel, ethyl acetate/hexane mixtures). Impure fractions (1.14 g) accounted for the low yield relative to L-hydroxyproline derivatives above. Elemental analysis for C17H22N2O7: Calculated C, 55.74; H, 6.05; N, 7.65. Found: Calculated C, 55.71; H, 6.08; N, 7.69.

Workup

  1. temperatureat reflux for 6 days

Sources & evidence

ORD record
ord-90a2ed9fa9b04dacaab11055533921ce
Source dataset
uspto-grants-2001_09
Patent number
US06288036B1

Reaction notes

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