tert-Butanol → 2-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one
Reaction equation
[OH:1][C:2]([CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8](SC)=[CH:7][CH:6]=1)=[O:4].O[O:16][S:17]([O-:19])=O.[K+].[C:21](O)(C)(C)C>C(Cl)Cl.O.CCOC(C)=O>[OH:1][C:2]([CH3:13])([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:17]([CH3:21])(=[O:19])=[O:16])=[CH:7][CH:6]=1)=[O:4]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
To a cold (4° C.) solution of 2-hydroxy-2-methyl-1-(4-(methylthio)phenyl)propan-1-one (45.0 g, 214 mmol, Step 2) in t-butanol (500 mL) and CH2Cl2 (500 mL) was added a solution of OXONE™ (194 g, 316 mmol) in water (1.4 L). The resulting suspension was stirred at r.t. for 18 h. The reaction was diluted with EtOAc (400 mL) and the layers were separated. The aqueous layer was extracted with EtOAc (2×250 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was dissolved in diethyl ether (250 mL), hexane was added (150 mL) an the product was swished for 2 h. The product was collected by filtration to give the title compound as a yellow solid.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted with EtOAc (2×250 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated in vacuo
- dissolutionThe crude product was dissolved in diethyl ether (250 mL)
- additionhexane was added (150 mL) an the product
- waitwas swished for 2 h
- filtrationThe product was collected by filtration
Sources & evidence
- ORD record
- ord-e6bf7f25f44147719edba9692569f1fd
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169188A
Reaction notes
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