Hydrochloric Acid → 2-Hydroxy-4'(methylthio)isobutyrophenone
Reaction equation
[CH3:1][CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].C(Cl)(Cl)(Cl)Cl.[OH-:19].[Na+].Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1.O.[Cl-].[Na+].O.CCOC(C)=O>[OH:19][C:2]([CH3:13])([CH3:1])[C:3]([C:5]1[CH:6]=[CH:7][C:8]([S:11][CH3:12])=[CH:9][CH:10]=1)=[O:4]Participants
10
Reactant 4
Product 1
Reagents, catalysts & solvents 5
Conditions
- Temperature
- 15 °C
Procedure
To a solution of 2-methyl-1-(4-(methylthio)phenyl)propan-1-one (28.5 g, 147 mmol, Step 1), Aliquat 336 (11.0 mL, 24 mmol) and carbon tetrachloride (21 mL, 218 mmol) in toluene (43 mL) was added sodium hydroxide (12.9 g, pellets, 322 mmol). The reaction was stirred at 15° C. for 2 h and then at r.t. for 16 h. The reaction was diluted with water (100 mL), brine (100 mL) and EtOAc (300 mL). The aqueous phase was acidified with 1N HCl and extracted with EtOAc (100 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel chromatography eluted with 15% EtOAc in hexane to give the title compound as a thick syrup.
Workup
- waitat r.t. for 16 h
- extractionextracted with EtOAc (100 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- customThe crude product was purified by silica gel chromatography
- washeluted with 15% EtOAc in hexane
Sources & evidence
- ORD record
- ord-1727940c555d4819ab9314896f83109f
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789413
Reaction notes
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