Hydroxyphenylacetic acid → Tert-butyl 2-(4-hydroxyphenyl)acetate
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:25](O)([CH3:28])([CH3:27])[CH3:26].N>O1CCCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:10])=[CH:6][CH:7]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
76.5 g (0.5 mols) of p-hydroxyphenylacetic acid was dissolved in 500 ml of tetrahydrofuran (THF). The resulting reaction solution was then cooled to a temperature of from −20° C. to −15° C. To the reaction solution was then added dropwise 231 g (1.1 mols) of trifluoroacetic anhydride. After the termination of dropwise addition, the reaction mixture was stirred at room temperature for 12 hours. The reaction solution was then again cooled to a temperature of from −20° C. to −15° C. To the reaction solution was then added dropwise 37 g (0.5 mols) of t-butanol. The reaction mixture was then stirred at room temperature for 3 hours. To the reaction solution was then added dropwise 100 ml of aqueous ammonia. The reaction mixture was then extracted with water to obtain t-butyl p-hydroxyphenylacetate.
Workup
- customThe resulting reaction solution
- temperaturewas then cooled to a temperature of from −20° C. to −15° C
- additionAfter the termination of dropwise addition
- temperatureThe reaction solution was then again cooled to a temperature of from −20° C. to −15° C
- stirringThe reaction mixture was then stirred at room temperature for 3 hours
- extractionThe reaction mixture was then extracted with water
Sources & evidence
- ORD record
- ord-76661f76723d43e989e2172d59638895
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06207343B1
Reaction notes
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