Hydrochloric Acid → Methyl alpha-methylthio-alpha-(m-benzoylphenyl)propionate
Reaction equation
CO.[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)OCC[O:18]2)[CH:12]=1)([CH3:10])[C:6]([O:8][CH3:9])=[O:7].Cl>O>[CH3:3][S:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:18])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:12]=1)([CH3:10])[C:6]([O:8][CH3:9])=[O:7]Participants
5
Procedure
Methanol (10 ml) and 1 ml of water were added to 2.52 g of methyl α-methylthio-α-[m-(2-phenyl-1,3-dioxa-2-cyclopentyl)phenyl]propionate, and 0.2 ml of conc. hydrochloric acid was added. The mixture was heated for 20 minutes under reflux. After cooling, 20 ml of water was added, and the mixture was extracted with 50 ml and 10 ml respectively of methylene chloride. The extract was washed twice with 10 ml of water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was chromatographed on a column of silica gel using methylene chloride as an eluent to afford 2.10 g of methyl α-methylthio-α-(m-benzoylphenyl)-propionate as a colorless oil in a yield of 95%.
Workup
- additionwas added
- temperatureThe mixture was heated for 20 minutes
- temperatureunder reflux
- temperatureAfter cooling
- extractionthe mixture was extracted with 50 ml and 10 ml respectively of methylene chloride
- washThe extract was washed twice with 10 ml of water
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customThe residue was chromatographed on a column of silica gel
Sources & evidence
- ORD record
- ord-c2898493bdba45d2a2fd105c3729f149
- Source dataset
- uspto-grants-1981_12
- Patent number
- US04308208
Reaction notes
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