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

HRID 1065050Notes

Reaction equation

HRID 1065050 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.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].N>C(O)C>[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

5

Reactant 3

HCID 222AmmoniaHCID 73972Sodium sulfide nonahydrateHCID 51429261-Methyl-4-[2-(4-nitrophenoxy)ethyl]benzene

Product 1

HCID 130176564-[2-(4-Methylphenyl)ethoxy]anilineYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[2-(4-Methylphenyl)ethoxy]nitrobenzene (VI) (5.14 g, 0.02 mole) and sodium sulfide nonahydrate (9.6 g, 0.04 mole) were added to a mixture of 95% aqueous ethanol (50 ml) and 29% aqueous ammonia (50 ml), followed by heating under reflux for 20 hours. Sulfur deposited was filtered while hot, and the filtrate was cooled, extracted with ether and treated in the same manner as in Example 17 to obtain 4.3 g of 4-[2-(4-methylphenyl)ethoxy]aniline (V) (yield, 95%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 hours
  3. filtrationSulfur deposited was filtered while hot, and the filtrate
  4. temperaturewas cooled
  5. extractionextracted with ether
  6. additiontreated in the same manner as in Example 17

Sources & evidence

ORD record
ord-8b0349ab18be48cdbd3e66426f3adc2e
Source dataset
uspto-grants-1982_05
Patent number
US04328166

Reaction notes

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