Hydroxylamine → Acetaminophen

HRID 1031780Notes

Reaction equation

HRID 1031780 reaction equation
[CH3:1][C:2]([NH:10][OH:11])=[C:3]1[CH:9]=[CH:8][C:6](=[O:7])[CH:5]=[CH:4]1.[CH3:12][C:13](C1C=CC(O)=CC=1)=[O:14].O[NH2:23]>S(Cl)(Cl)=O>[C:13]([NH:23][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[CH:8][CH:9]=1)(=[O:14])[CH3:12].[CH3:1][C:2]([NH:10][OH:11])=[C:3]1[CH:9]=[CH:8][C:6](=[O:7])[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 74694'-HydroxyacetophenoneHCID 178465686HCID 178465686, compound

Product 2

HCID 1983AcetaminophenHCID 178465686HCID 178465686, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideCatalyst

Procedure

N-acetyl-para-aminophenol is prepared by subjecting 4-hydroxyacetophenone oxime to a Beckmann rearrangement in the presence of a thionyl chloride catalyst and an alkyl alkanoate as the reaction solvent. An integrated process is disclosed wherein 4-hydroxyacetophenone is reacted with a hydroxyl amine salt and a base to obtain the ketoxime of the ketone, e.g., 4-hydroxyacetophenone oxime, extracting the ketoxime product from the reaction with alkanoate ester and subjecting the ketoxime dissolved in the ester to a Beckmann rearrangement in the presence of a thionyl chloride catalyst.

Sources & evidence

ORD record
ord-3903472bc64645ea83d4146d4538adb7
Source dataset
uspto-grants-1990_09
Patent number
US04954652

Reaction notes

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