Benzaldehyde → HCID 53914774, compound

HRID 614246Notes

Reaction equation

HRID 614246 reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].CO.[OH-].C[N+](C)(C)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)C1C=CC=CC=1>C(Cl)Cl.O1CCCC1>[CH3:6][S:4]([C:3]([S:2][CH3:1])=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:5]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 66854Benzyltrimethylammonium hydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 53914774HCID 53914774, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

FAMSO (2.572 g), 3 ml of a 40% methanol solution of trimethylbenzylammonium hydroxide, and 3 ml of benzaldehyde were added to 5 ml of tetrahydrofuran, and the mixture was refluxed for 4 hours. After adding 100 ml of methylene chloride, the reaction mixture was washed with dilute sulfuric acid. The product was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel using methylene chloride as an eluant to afford 3.994 g of 1-methylsulfinyl-1-methylthio-2-phenylethylene as a colorless liquid having a boiling point of 149° to 150° C./0.08 mmHg in a yield of 91.0%.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. washthe reaction mixture was washed with dilute sulfuric acid
  3. dry with materialThe product was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-1c66ada6ec4c4728969aa3fc5e451bd0
Source dataset
uspto-grants-1979_03
Patent number
US04144248

Reaction notes

Loading…