Water → Decyl 4-nitrophenyl ether

HRID 902826Notes

Reaction equation

HRID 902826 reaction equation
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.[CH2:11](I)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:11]([O:10][C:3]1[CH:4]=[CH:5][C:6]([N+:7]([O-:9])=[O:8])=[CH:1][CH:2]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 163141-Iododecane

Product 1

HCID 141653Decyl 4-nitrophenyl etherYield 110%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

At the outset, p-nitrophenol 1 (13.4 g, 96 mmol) and n-decyl iodide (25 g, 93 mmol) were dissolved in DMF (100 ml) to prepare a solution. Potassium carbonate (12.9 g) was added to the solution, and the mixture was stirred at 100° C. for about 2 hr. After the disappearance of the starting material was confirmed by TLC, the reaction mixture was allowed to cool to room temperature. Upon the addition of water and salt in an ice bath, solid matter was precipitated, and the solid was collected by filtration to give 4-decyloxynitrobenzene 2 (28.28 g, 110%) as a light yellow liquid.

Workup

  1. customto prepare a solution
  2. temperatureto cool to room temperature
  3. customsolid matter was precipitated
  4. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-3668ef34b6244773b74bdd907aaabb4a
Source dataset
uspto-grants-2008_04
Patent number
US07365359B2

Reaction notes

Loading…