Hydrochloric Acid → 4-[2-(4-Methylphenyl)ethoxy]aniline

HRID 1065048Notes

Reaction equation

HRID 1065048 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.Cl.[OH-].[Na+]>C(O)C.[Fe]>[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene

Product 1

HCID 130176564-[2-(4-Methylphenyl)ethoxy]anilineYield 90.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

4-[2-(4-Methylphenyl)ethoxy]nitrobenzene (VI) (5.14 g, 0.02 mole) and iron powder (6.7 g, 0.12 mole) were added to 50% aqueous ethanol (50 ml), and a solution of conc. hydrochloric acid (1 ml) in 50% aqueous ethanol (10 ml) was added dropwise thereto over 15 minutes with stirring under reflux. After heating under reflux for an additional 2 hours, the reaction mixture was cooled, neutralized with a dilute aqueous sodium hydroxide solution and extracted with ether. The ether layer was washed with water, dried over anhydrous potassium carbonate, concentrated and distilled to obtain 4.1 g of 4-[2-(4-methylphenyl)ethoxy]aniline (V) (yield, 90.3%).

Workup

  1. temperatureunder reflux
  2. temperatureAfter heating
  3. temperatureunder reflux for an additional 2 hours
  4. temperaturethe reaction mixture was cooled
  5. extractionextracted with ether
  6. washThe ether layer was washed with water
  7. dry with materialdried over anhydrous potassium carbonate
  8. concentrationconcentrated
  9. distillationdistilled

Sources & evidence

ORD record
ord-5fa5bd2f569b419d9cf6a81579249ce1
Source dataset
uspto-grants-1982_05
Patent number
US04328166

Reaction notes

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