Water → 1-Methylsulfinyl-1-methylthio-2-(p-isobutylphenyl)ethylene

HRID 1733610Notes

Reaction equation

HRID 1733610 reaction equation
[CH2:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH3:13][S:14][CH2:15][S:16](=[O:18])[CH3:17].CC(C)([O-])C.[K+].O>C(O)(C)(C)C.C(Cl)Cl>[CH3:17][S:16]([C:15]([S:14][CH3:13])=[CH:9][C:8]1[CH:11]=[CH:12][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=1)=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 577537Benzaldehyde, 4-(2-methylpropyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 545626121-Methylsulfinyl-1-methylthio-2-(p-isobutylphenyl)ethyleneYield 87.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent2×

Procedure

A mixture of 486 mg of p-isobutylbenzaldehyde and 450 mg of formaldehyde dimethyl mercaptal S-oxide was dissolved in 1 ml of t-butanol, and 2.0 ml of a t-butanol solution (0.608 N) of potassium t-butoxide was added. The mixture was stirred for 12 hours at room temperature. Water (0.5 ml) was added to the reaction mixture, and then 50 ml of methylene chloride was added. The mixture was dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure. The oily residue was chromatographed on a column of silica gel using methylene chloride as an eluent to afford 701 mg of 1-methylsulfinyl-1-methylthio-2-(p-isobutylphenyl)ethylene in a yield of 87%.

Workup

  1. dry with materialThe mixture was dried over anhydrous sodium sulfate
  2. customThe drying agent was separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe oily residue was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-6a0c49bcb00448029185052492f5e359
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

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