3-Nitrophenol → 3-[2-(Cyclohexyloxy)ethoxy]nitrobenzene

HRID 1701809Notes

Reaction equation

HRID 1701809 reaction equation
[O-]CC.[Na+].[N+:5]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)([O-:7])=[O:6].C1(C)C=CC(S(O[CH2:25][CH2:26][O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)(=O)=O)=CC=1>CN(C)C=O.O>[CH:28]1([O:27][CH2:26][CH2:25][O:14][C:10]2[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[CH:13]=[CH:12][CH:11]=2)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 111373-NitrophenolHCID 2723922Sodium ethoxideHCID 113809922-(Cyclohexyloxy)ethyl 4-methylbenzene-1-sulfonate

Product 1

HCID 155830783-[2-(Cyclohexyloxy)ethoxy]nitrobenzeneYield 95.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6.8 g of sodium ethoxide and 15 g of m-nitrophenol in 250 ml of dimethylformamide, 28 g of cyclohexyloxyethyl p-toluenesulfonate were added. After heating at 100° C. for 2 hours, the resulting mixture was diluted with water and extracted with benzene. The solvent was removed under reduced pressure, and the residue was purified by vacuum distillation to give 23.8 g of 3-[2-(cyclohexyloxy)ethoxy]nitrobenzene. B.P., 118°-124° C./0.1 mmHg. nD27 1.5380.

Workup

  1. extractionextracted with benzene
  2. customThe solvent was removed under reduced pressure
  3. distillationthe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-4b49e88f7b8e443fb09dab50b3d7cb1f
Source dataset
uspto-grants-1983_04
Patent number
US04378992

Reaction notes

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