Acetone → 4-[2-(4-Methylphenyl)ethoxy]aniline

HRID 1065049Notes

Reaction equation

HRID 1065049 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+].[S].CC(C)=O>O.CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzeneHCID 5362487Sulfur

Product 1

HCID 130176564-[2-(4-Methylphenyl)ethoxy]anilineYield 96.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

4-[2-(4-Methylphenyl)ethoxy]nitrobenzene (VI) (5.14 g, 0.02 mole), sodium hydroxide powder (3.0 g) and sulfur (1.6 g, 0.05 mole) were added to a mixture of acetone (20 ml) and methanol (20 ml), followed by heating under reflux for 5 hours. After cooling, the reaction mixture was diluted with water, extracted with ether and treated in the same manner as in Example 18 to obtain 4.4 g of 4-[2-(4-methylphenyl)ethoxy]aniline (V) (yield, 96.9%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. additiontreated in the same manner as in Example 18

Sources & evidence

ORD record
ord-bf58e061715b4681a929a2fc19b2547d
Source dataset
uspto-grants-1982_05
Patent number
US04328166

Reaction notes

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