Acetic Acid → 4'-Hydroxyacetophenone

HRID 365021Notes

Reaction equation

HRID 365021 reaction equation
F.[C:2]1([OH:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](O)(=[O:11])[CH3:10]>>[OH:8][C:2]1[CH:7]=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 996PhenolHCID 14917Hydrofluoric Acid

Product 1

HCID 74694'-HydroxyacetophenoneYield 40%

Procedure

Simons et al, Journal of the American Chemical Society, 61, 1795 and 1796 (1939) teach the acylation of aromatic compounds using hydrogen fluoride as a condensing agent and in Table 1 on page 1796 show the acetylation of phenol with acetic acid to produce p-hydroxyacetophenone (4-HAP) in 40% yield.

Sources & evidence

ORD record
ord-e8c67cef5b4742a8821915cf681d9324
Source dataset
uspto-grants-1986_08
Patent number
US04607125

Reaction notes

Loading…