(2-Methylsulfanylphenyl)methanol → 2-(Methylthio)benzaldehyde

HRID 1821349Notes

Reaction equation

HRID 1821349 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[O:10]

Participants

4

Reactant 2

HCID 3551404(2-Methylsulfanylphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 2864432-(Methylthio)benzaldehydeYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methylsulfanylphenyl)methanol (0.20 g, 1.3 mmol) obtained in Step 1 in dichloromethane (4.0 mL), Celite (0.40 g) and pyridinium chlorochromate (0.42 g, 1.9 mmol) were added, followed by stirring at room temperature for 1.0 hour. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain 2-methylsulfanylbenzaldehyde (0.14 g, 69%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-865e7276031540db982582d971c674f7
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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