Methanol → HCID 54558564, compound

HRID 614248Notes

Reaction equation

HRID 614248 reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].[O:7]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.[OH-].C[N+](C)(C)CC1C=CC=CC=1>O1CCCC1.C(Cl)Cl>[CH3:6][S:4]([C:3]([S:2][CH3:1])=[CH:17][C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=1)=[O:5]

Participants

7

Reactant 4

HCID 887MethanolHCID 382843-PhenoxybenzaldehydeHCID 66854Benzyltrimethylammonium hydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 54558564HCID 54558564, compoundYield 61.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

FAMSO (1.27 g) and 2.00 g of m-phenoxybenzaldehyde were dissolved in 10 ml of tetrahydrofuran, and 1 ml of a 40% methanol solution of trimethylbenzylammonium hydroxide was added. The mixture was heated under reflux for 26 hours. Methylene chloride (50 ml) was added, and the reaction mixture was washed with 3N dilute sulfuric acid. The product was dried over anhydrous potassium carbonate, concentrated under reduced pressure, and chromatographed on a silica gel column using methylene chloride as an eluant to afford 1.88 g of 1-methylsulfinyl-1-methylthio-2-(m-phenoxyphenyl)ethylene as a colorless oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 26 hours
  3. washthe reaction mixture was washed with 3N dilute sulfuric acid
  4. dry with materialThe product was dried over anhydrous potassium carbonate
  5. concentrationconcentrated under reduced pressure
  6. customchromatographed on a silica gel column

Sources & evidence

ORD record
ord-41d349729fdb446f9582b21806456bac
Source dataset
uspto-grants-1979_03
Patent number
US04144248

Reaction notes

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