1-Chloro-4-nitrobenzene → 1-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene

HRID 444175

Reaction equation

HRID 444175 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=1)([O-:15])=[O:14]>CS(C)=O>[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][O:12][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 952944-Methylphenethyl alcohol

Product 1

HCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzeneYield 89.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 65% sodium hydride (1.1 g, 0.03 mole) in dimethylsulfoxide (30 ml) were added 2-(4-methylphenyl)ethyl alcohol (VIII) (2.72 g, 0.02 mole) and 4-nitrochlorobenzene (IX: X=Cl) (3.15 g, 0.02 mole). After heating to 30° C. for 5 hours with stirring, the reaction mixture was treated in the same manner as in Example 12 to obtain 4.6 g of 4-[2-(4-methylphenyl)ethoxy]nitrobenzene (VI) as white crystals (yield, 89.5%).

Workup

  1. additionthe reaction mixture was treated in the same manner as in Example 12
  2. customto obtain

Sources & evidence

ORD record
ord-68c853b477e7413a8acfb7aa86d78478
Source dataset
uspto-grants-1981_04
Patent number
US04263219

Linked notes

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