4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-
Reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OC1C=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1>S(=O)(=O)(O)O>[C:5]([O:4][C:1]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:2]=1)(=[O:7])[CH3:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
For example, 500 grams of acetic anhydride and 2 drops of sulfuric acid are placed in a vessel and 274 grams of p-hydroxy benzoic acid are added with stirring. The contents of the vessel are stirred at 100°C. for 1 hour, and are cooled to about 15°C. The p-acetoxy benzoic acid formed is recovered by pouring the hot acetic anhydride solution over an ice/water mixture, removing the product by filtration, washing the same with deionized water in a high shear mixer, and drying in a forced air oven. A like quantity of m-acetoxy benzoic acid is formed in an identical manner utilizing m-hydroxy benzoic acid as one of the reactants.
Workup
- stirringThe contents of the vessel are stirred at 100°C. for 1 hour
Sources & evidence
- ORD record
- ord-63b5d5d9e1c9424c929f9a38cd950901
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03948856
Reaction notes
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