Sodium borohydride → 2-Hydroxy-3-(o-tolylthio)benzyl alcohol

HRID 1164107Notes

Reaction equation

HRID 1164107 reaction equation
[BH4-].[Na+].[OH:3][C:4]1[C:11]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]>CO>[OH:3][C:4]1[C:11]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 130666712-Hydroxy-3-(o-tolylthio)benzaldehyde

Product 1

HCID 130666702-Hydroxy-3-(o-tolylthio)benzyl alcoholYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (850 mg) was added slowly to a suspension of 2-hydroxy-3-(o-tolylthio)benzaldehyde (11 g) in methanol (50 ml) at temperature below 15° C., and the mixture was stirred at the same temperature for 15 minutes and then at room temperature for 30 minutes. Methanol was distilled off from the reaction mixture under reduced pressure, and the residue was dissolved in water, acidified with conc. hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried and evaporated under reduced pressure. The residue was crystallized with aqueous ethanol to give 2-hydroxy-3-(o-tolylthio)benzyl alcohol (8.45 g), mp. 75°-77° C.

Workup

  1. waitat room temperature for 30 minutes
  2. distillationMethanol was distilled off from the reaction mixture under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was crystallized with aqueous ethanol

Sources & evidence

ORD record
ord-492f5b2dd853418b84394fb01ae9b39f
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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