Acetic Acid → t-Butyl-4-hydroxy-phenyl acetate
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([O:12]C)[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].S(=O)(=O)(O)O.[C:19](O)(=[O:21])[CH3:20]>>[C:19]([O:11][C:10]1[CH:9]=[CH:8][C:7]([OH:12])=[CH:6][C:5]=1[C:1]([CH3:2])([CH3:3])[CH3:4])(=[O:21])[CH3:20]Participants
Procedure
To 36 g of 3-t-butyl-4-hydroxyanisole dissolved in 100 ml of anhydrous acetic acid was added a catalytic amount of concentrated sulfuric acid and the mixture was stirred at room temperature for 6 days. After the reaction solution was concentrated under reduced pressure, the concentrate was dissolved in 200 ml of acetonitrile and combined with 60 g of sodium iodide. To the resulting solution was added dropwise 51 ml of trimethylsilyl chloride at room temperature and then the mixture was heated under reflux for 3 hours. The reaction mixture was allowed to attain room temperature, and then concentrated under reduced pressure, combined with water and extracted with ethyl acetate. The extracted layers were washed with saturated brine, then dried over anhydrous magnesium sulfate and concentrated to give 47.0 g of 4-acetoxy-3-t-butylphenol as a colorless oil (quantitative).
Workup
- concentrationAfter the reaction solution was concentrated under reduced pressure
- dissolutionthe concentrate was dissolved in 200 ml of acetonitrile
- additionTo the resulting solution was added dropwise 51 ml of trimethylsilyl chloride at room temperature
- temperaturethe mixture was heated
- temperatureunder reflux for 3 hours
- customto attain room temperature
- concentrationconcentrated under reduced pressure
- extractionextracted with ethyl acetate
- washThe extracted layers were washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b9179fe6b48c4bd099f14e0d0e576a31
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686389B2
Reaction notes
Loading…