Acetic Acid → 4'-Hydroxyacetophenone

HRID 1248471Notes

Reaction equation

HRID 1248471 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

4

Reactant 3

HCID 176Acetic AcidHCID 996PhenolHCID 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 at 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-f364354bd77a49478bc02a804c1e437e
Source dataset
uspto-grants-1985_06
Patent number
US04524217

Reaction notes

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