Phenol → Phenyl acetate
Reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](Cl)(=[O:10])[CH3:9]>>[C:8]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:10])[CH3:9]Participants
Reactant 2
Product 1
Procedure
Phenol was acetylated with a 1.5 times molar excess of acetyl chloride at room temperature, the excess acetyl chloride being removed by evaporation under reduced pressure. A very high yield of phenyl acetate was produced. To this reaction product a 2.4 times molar excess of acetic anhydride was added with stirring, followed by a 1.5 times molar excess of sulphuric acid added dropwise at 50° C. over 30 minutes. After stirring for a further 60 minutes, the mixture was neutralised using a 1.5 time molar excess of sodium acetate in glacial acetic acid solution. Trituration of the reaction mixture with ether followed by filtration resulted in a dry yellow solid. This was recrystallised from methanol and washed with sodium carbonate solution. A 99% conversion to sodium sulphonatophenyl acetate was achieved.
Workup
- customthe excess acetyl chloride being removed by evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-2ee52d7e70ed4c5c9b2942a76dabeaa6
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04788316
Reaction notes
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