Phenol → 4'-Hydroxyacetophenone

HRID 638385Notes

Reaction equation

C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=O)C.[C:11]1([OH:17])C=CC=C[CH:12]=1>>[CH3:12][C:11]([C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1)=[O:17]

Participants

Reactant 2

HCID 996Phenol

HCID 31229Phenyl acetate

Product 1

HCID 74694'-Hydroxyacetophenone

Procedure

4-Acetoxyacetanilide is produced by subjecting phenyl acetate to a Fries rearrangement or phenol and an acetylating agent to a Friedel-Crafts acetylation to form 4-hydroxyacetophenone which is then reacted with hydroxylamine or a hydroxylamine salt to form 4-hydroxyacetophenone oxime. The oxime is then subjected to a Beckmann rearrangement and accompanying acetylation with acetic anhydride to form the 4-acetoxyacetanilide.

Sources & evidence

ORD record: ord-e1216cb6172d4cf8a805854b43b4d365
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04560789

Reaction notes

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