2-(3-(Hydroxymethyl)phenylthio)ethanol → 3-(2-Hydroxyethylthio)benzaldehyde

HRID 446382Notes

Reaction equation

HRID 446382 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([S:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:7][CH:8]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[OH:12][CH2:11][CH2:10][S:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH:2]=[O:1]

Participants

4

Reactant 1

HCID 579893042-(3-(Hydroxymethyl)phenylthio)ethanol2×

Product 1

HCID 579891823-(2-Hydroxyethylthio)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (1.36 g) was added to a solution of 2-(3-(hydroxymethyl)phenylthio)ethanol [Aromatic Intermediate 16, step b] (0.29 g) in DCM (10 mL). The resulting mixture was heated at reflux for 4 h, cooled and filtered through Celite. The filter pad was washed with DCM (3×20 mL). The filtrate and washing were combined and evaporated to give the subtitled compound as a yellow gum. Yield 0.2 g.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 h
  3. temperaturecooled
  4. filtrationfiltered through Celite
  5. washThe filter pad was washed with DCM (3×20 mL)
  6. washThe filtrate and washing
  7. customevaporated

Sources & evidence

ORD record
ord-f0c9e049be8f41e4a46542c9d45db6fe
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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