4-Aminophenol → 4-Ethoxyaniline

HRID 1703508Notes

Reaction equation

HRID 1703508 reaction equation
CO[CH2:3][CH2:4][O:5][CH2:6][CH2:7]OC.C(Cl)C.C[O-].[Na+].OC1C=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>CO>[CH2:4]([O:5][C:6]1[CH:7]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)[CH3:3]

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 6337ChloroethaneHCID 8150DiglymeHCID 10942334Sodium Methoxide

Product 1

HCID 90764-EthoxyanilineYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In accordance with the process of Example 2, 150 ml of diethyleneglycol dimethyl ether, 19.3 g (0.3 mole) of ethyl chloride, 42.2 g (0.22 mole) of sodium methylate in 28% methanol solution and 21.8 g (0.2 mole) of p-hydroxyaniline were charged in the autoclave and the reaction was carried out at 80° C. for 6 hours with stirring to obtain 19.7 g of p-ethoxyaniline having a boiling point of 135° to 136° C./24 mmHg. (yield: 72.1%).

Sources & evidence

ORD record
ord-453885475f5a44caa8c0c0d13e86618f
Source dataset
uspto-grants-1978_11
Patent number
US04124640

Reaction notes

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