4-(Methylthio)benzaldehyde → [4-(Methylsulfanyl)phenyl]methanol

HRID 862860Notes

Reaction equation

HRID 862860 reaction equation
[BH4-].[Na+].[CH3:3][S:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1>C(O)(C)C>[CH3:3][S:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 769854-(Methylthio)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 592968[4-(Methylsulfanyl)phenyl]methanolYield 98.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Sodium borohydride (3.78 g) was added to isopropyl alcohol (50 ml) and the mixture was stirred under ice-cooling. Thereto was dropwise added 4-(methylthio)benzaldehyde (15 g) and the mixture was stirred at room temperature for 30 minutes. The solvent was distilled away and water was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away and the residue obtained was recrystallized from hexane-ethyl acetate to give the subject compound (15 g) as white crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationThe solvent was distilled away
  4. additionwater was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled away
  9. customthe residue obtained
  10. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c1789a407d224bd58e7e129981a754dc
Source dataset
uspto-grants-1998_02
Patent number
US05719176

Reaction notes

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