Benzoic acid, 4-(acetyloxy)- → 4'-Hydroxyacetophenone
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10]C(C)=O)=[CH:6][CH:5]=1)=[O:3].C(OC1C=CC(C(O)=O)=CC=1)(=O)C>>[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3]Participants
3
Procedure
The 4-acetoxyacetophenone (4-AAP) used as the starting material for the catalytic oxidation to 4-acetoxybenzoic acid may be obtained as a co-product with the 4-hydroxyacetophenone (4-HAP) produced by the Fries rearrangement of phenyl acetate or the Friedel-Crafts acetylation of phenol, e.g., when the reaction is carried out in the presence of HF and an acid anhydide, or it may be produced from the 4-HAP by reacting the latter with an acetylating agent such as acetic anhydride, as indicated by equation (III), by contacting the 4-HAP with, for example, about 1 to 5 moles of the anhydride per mole of 4-HAP at a temperature, for example, in the range of 120° to 140° C. for a period, for example, in the range of 1 to 4 hours.
Sources & evidence
- ORD record
- ord-b2761c3277664900868a91d0c8f671bf
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04665215
Reaction notes
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