4-Nitrophenol → 4-(2-Chloroethoxy)aniline

HRID 1578551Notes

Reaction equation

HRID 1578551 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-])=O.[Cl:13][CH2:14][CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O>O>[Cl:13][CH2:14][CH2:15][O:12][C:9]1[CH:10]=[CH:11][C:6]([NH2:3])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium Hydroxide2×

Product 1

HCID 1196994-(2-Chloroethoxy)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

42 grams (1.05 mole) of sodium hydroxide were dissolved in 75 milliliters of water, and 139 grams (1 mole) of 4-nitrophenol and 235 grams (1 mole) of β-chloroethyl-p-toluene sulfonate were added, while stirring. Subsequently the reaction mixture was heated at 100°C for 4 hours. After cooling, the mixture was made alkaline by means of a solution of sodium hydroxide of 33 % strength and was diluted with about 5 liters of water. The precipitated crystalline product was filtered off with suction, washed with water and dried.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitated crystalline product was filtered off with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-d292a114797943a7af9e18091741b3dd
Source dataset
uspto-grants-1976_02
Patent number
US03937726

Reaction notes

Loading…