4-Hydroxybenzaldehyde → 4-Cyanophenol

HRID 1263210Notes

Reaction equation

HRID 1263210 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.Cl.[NH2:11]O.C1(C)C=CC=CC=1.O>CC(CC(C)=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)#[N:11]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 1140TolueneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 130194-CyanophenolYield 91%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

503 Milligrams of p-hydroxybenzaldehyde, 323 mg of hydroxylamine hydrochloride and 10 ml of toluene were introduced to a flask of 50 ml, equipped with a Dean-Stark dehydrating apparatus. The reaction mixture was stirred under reflux for 4 hrs. After the reaction finished, water and MIBK were added to the reaction mixture and mixed, followed by separation into two layers. Aqueous layer was extracted again by MIBK and the extract was combined with toluene layer first separated and subjected to the analysis of the products by gaschromatography [5% PEG 20M, 0.5 m, 190° C. (4 minutes retention)→220° C. (5 minutes retention), 2° C./min]. From the results, it was found that the conversion of p-hydroxybenzaldehyde was 100% and 449 mg (91% yield) of p-cyanophenol and 6.1 mg (1.1% yield) of p-hydroxybenzaldoxime were produced.

Workup

  1. customequipped with a Dean-Stark
  2. temperatureunder reflux for 4 hrs
  3. additionmixed
  4. customfollowed by separation into two layers
  5. extractionAqueous layer was extracted again by MIBK
  6. customfirst separated
  7. customsubjected to the analysis of the products by gaschromatography [5% PEG 20M, 0.5 m, 190° C. (4 minutes retention)→220° C. (5 minutes retention), 2° C./min]

Sources & evidence

ORD record
ord-69d60957d0db4cf481b2f1960d703776
Source dataset
uspto-grants-1984_06
Patent number
US04456562

Reaction notes

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