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Sodium Hydroxide → 1-Methylsulfinyl-1-methylthio-2-(m-benzoylphenyl)ethylene

HRID 614251
Notes
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Reaction equation

HRID 614251 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][S:18][CH2:19][S:20]([CH3:22])=[O:21].[OH-].[Na+]>O>[CH3:22][S:20]([C:19]([S:18][CH3:17])=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 130201683-Benzoylbenzaldehyde

Product 1

HCID 541901371-Methylsulfinyl-1-methylthio-2-(m-benzoylphenyl)ethylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

m-Benzoylbenzaldehyde (902 mg) was added to 1 ml of FAMSO, and 60 mg of sodium hydroxide was added. The mixture was stirred at 95° C. for 70 minutes in an atmosphere of argon. Water (20 ml) was added, and the reaction mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and chromatographed on a silica gel column using methylene chloride as an eluant to afford 1.035 g of 1-methylsulfinyl-1-methylthio-2-(m-benzoylphenyl)ethylene.

Workup

  1. additionwas added
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-cbd5e9837fc14945a2503c53069e1c2a
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04144248

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes