4'-Hydroxyacetophenone → 4-Methylphenyl acetate

HRID 653228

Reaction equation

HRID 653228 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:11][C:12]([C:14]1[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=1)=[O:13].[OH:21][CH2:22][C:23](C1C=CC=CC=1)=O>F>[C:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[CH:6]=1)(=[O:3])[CH3:2].[C:22]([O:20][C:17]1[CH:18]=[CH:19][C:14]([CH3:12])=[CH:15][CH:16]=1)(=[O:21])[CH3:23].[C:1]([O:4][C:5]1[C:10]([O:13][CH3:12])=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 74694'-HydroxyacetophenoneHCID 31229Phenyl acetateHCID 68490alpha-Hydroxyacetophenone

Product 3

HCID 87974-Methylphenyl acetateHCID 61155Guaiacyl acetateHCID 67406Cresatin

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent2×

Procedure

Dann and Mylius in a dissertation included as part of a series of Reports from the Institute for Applied Chemistry of the University of Erlangen, received for publication on Jan. 7, 1954 and published in Annalen der Chemie 587 Band, pages 1 to 15, show the rearrangement of phenyl acetate in hydrogen fluoride to 4-hydroxyacetophenone, with a maximum yield of 81% after 24 hours of reaction time. They also report a yield of 92% from this reaction stated to be obtained by K. Weichert as reported in Angewandte Chemie 56, 338 (1943), but suggest that the difference in yields may be at least partly due to the previous ignoring by Weichert of the accompanying 2-hydroxyacetophenone. Dann and Mylius also report somewhat lower yields of hydroxy aromatic ketones from rearrangements in hydrogen fluoride of m-cresyl acetate, p-cresyl acetate, and guaiacol acetate.

Workup

  1. customwith a maximum yield of 81% after 24 hours of reaction time
  2. customto be obtained by K
  3. customin yields may

Sources & evidence

ORD record
ord-d40068c51f3f4e71b8bf550b2095608a
Source dataset
uspto-grants-1987_06
Patent number
US04675449

Linked notes

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