4-Nitrosophenol → 5990-80-7

HRID 1611074Notes

Reaction equation

HRID 1611074 reaction equation
[CH3:1][Si:2]([O:9][CH2:10][CH3:11])([O:6][CH2:7][CH3:8])OCC.[CH3:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].N([C:21]1C=CC(O)=CC=1)=O>C(OCC)C>[CH:13]([C:14]1[CH:21]=[CH:18][C:17]([Si:2]([CH3:1])([O:6][CH2:7][CH3:8])[O:9][CH2:10][CH3:11])=[CH:16][CH:15]=1)=[CH2:12]

Participants

5

Reactant 3

HCID 77294-NitrosophenolHCID 8900HeptaneHCID 16241Triethoxymethylsilane

Product 1

HCID 112418525990-80-7Yield 70.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
2 °C

Procedure

A, is slowly added dropwise in order to achieve a permanent exothermal reaction. The solvent is stirred under reflux at ambient pressure. After termination of said exothermal reaction, the reaction mixture is cooled down to 2° C., and subsequently, 155.5 g (872 mmol) methyl triethoxysilane in 160 ml dry diethyl ether is added; the temperature should not substantially exceed 15° C. After termination of the substitution reaction, stirring is continued over night at ambient temperature. Subsequently, about 200 ml n-heptane is added to obtain a precipitation of the magnesium salts. The magnesium salts are separated by filtration, 5.4 g (0.44 mmol) 4-nitrosophenol is added to the filtrate, the solvent is removed in a rotary evaporator, and the residue is subjected to a fractionating distillation under vacuum. 72.5 g (307 mmol) of the product was obtained.

Workup

  1. additionA, is slowly added dropwise in order
  2. customa permanent exothermal reaction
  3. temperatureunder reflux at ambient pressure
  4. customAfter termination of said exothermal reaction
  5. customsubstantially exceed 15° C
  6. customAfter termination of the substitution reaction
  7. stirringstirring
  8. waitis continued over night at ambient temperature
  9. customto obtain
  10. customa precipitation of the magnesium salts
  11. additionis added to the filtrate
  12. customthe solvent is removed in a rotary evaporator
  13. distillationthe residue is subjected to a fractionating distillation under vacuum

Sources & evidence

ORD record
ord-b7a27deeabeb4f89af78a06dc3f13040
Source dataset
uspto-grants-2006_01
Patent number
US06984747B2

Reaction notes

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