Benzyl Chloride → HCID 12219896, compound
Reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].O1CCCC1.[H-].[Na+].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O.C(Cl)Cl>[CH3:1][S:2][CH:3]([S:4]([CH3:6])=[O:5])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
7
Procedure
590 mg of methyl methylthiomethyl sulfoxide was dissolved in 5 ml. of tetrahydrofuran, and under cooling with ice, 171 mg (1.5 equivalents) of sodium hydride was added. The mixture was stirred for 1 hour. 813 mg of benzyl chloride was added, and the mixture was stirred at room temperature for 15 hours. 50 ml of methylene chloride and 1 ml. of water were added, and the reaction mixture was dried with anhydrous sodium sulfate, and the organic layer was concentrated at reduced pressure. The residue was subjected to column chromatography (silica gel, methylene chloride and ethyl acetate) to give 659 mg of methyl 1-methylthio-2-phenylethyl sulfoxide in a conversion yield of 92.2%.
Workup
- additionwas added
- stirringthe mixture was stirred at room temperature for 15 hours
- dry with materialthe reaction mixture was dried with anhydrous sodium sulfate
- concentrationthe organic layer was concentrated at reduced pressure
Sources & evidence
- ORD record
- ord-b78873dee7d543aba54b73ece1c95f34
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962281
Reaction notes
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