Benzyl Chloride → HCID 12219896, compound

HRID 1657878Notes

Reaction equation

HRID 1657878 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]=1

Participants

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

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 15 hours
  3. dry with materialthe reaction mixture was dried with anhydrous sodium sulfate
  4. 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

Loading…