1-Chloro-4-nitrobenzene → 4-Nitrophenol

HRID 1263013Notes

Reaction equation

HRID 1263013 reaction equation
ClC1C=CC([N+](=NC2C=CC(Cl)=CC=2)[O-:9])=CC=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.C(OC1C=CC(N=NC2C=CC(OCC)=CC=2)=CC=1)C>>[CH:21]1[C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=[C:19]([OH:9])[CH:20]=1

Participants

4

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 119604,4'-DichloroazoxybenzeneHCID 101783Diazene, bis(4-ethoxyphenyl)-

Product 1

HCID 9804-NitrophenolYield 95%

Procedure

It has now been found that p-nitrophenetole is obtained with excellent purity and high yields by reaction of p-chloronitrobenzene with ethanol and alkali metal hydroxide in the presence of a phase transfer catalyst, when the reaction is carried out at a temperature in the range of from 60° to 80° C. Thus, a product having a melting point of 58°-59.5° C. and being free from 4,4'-dichloroazoxybenzene, p-chloronitrobenzene, 4,4'-diethoxyazobenzene and p-nitrophenol is obtained with a yield of about 95%.

Workup

  1. customis carried out at a temperature in the range of from 60° to 80° C

Sources & evidence

ORD record
ord-9845cd312133482ab4966b72b8150927
Source dataset
uspto-grants-1984_06
Patent number
US04454355

Reaction notes

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