Acetic Acid → 4'-Hydroxyacetophenone

HRID 2309124Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F.[C:9](O)(=[O:11])[CH3:10]>>[CH3:10][C:9]([C:4]1[CH:3]=[CH:2][C:1]([OH:7])=[CH:6][CH:5]=1)=[O:11]

Participants

Reactant 3

HCID 176Acetic Acid

HCID 996Phenol

HCID 14917Hydrofluoric Acid

Product 1

HCID 74694'-HydroxyacetophenoneYield 61.6%

Procedure

Dann and Mylius also disclose the reaction of phenol and glacial acetic acid in the presence of hydrogen fluoride to produce 4-hydroxyacetophenone in a yield of 61.6%. This reaction may be conventionally characterized as a Friedel-Crafts acetylation of phenol with acetic acid as the acetylating agent.

Sources & evidence

ORD record: ord-4fdafa71ab7b4a45b40e840381fa5ce9
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04692546

Reaction notes

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