Hydrochloric Acid → [3-Methyl-4-(methylthio)phenyl]methanol

HRID 1006505Notes

Reaction equation

HRID 1006505 reaction equation
[BH4-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[S:12][CH3:13])[CH:7]=[O:8].Cl>C(O)C>[CH3:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:9]=[CH:10][C:11]=1[S:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 226713353-Methyl-4-(methylthio)benzaldehyde

Product 1

HCID 22671310[3-Methyl-4-(methylthio)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (1.40 g, 0.037 mol) was added to an ice-bath cooled solution of the product of example 28 step a) (6.16 g, 0.037 mol) in ethanol (50 ml). After 1 hour, the reaction mixture was neutralised by careful addition of aqueous hydrochloric acid (2 molar) and concentrated in vacuo to remove the organic solvent. The remaining aqueous solution was then extracted with ethyl acetate (×3). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to yield the sub-title compound as a brown oil (6 g) in quantitative yield.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove the organic solvent
  3. extractionThe remaining aqueous solution was then extracted with ethyl acetate (×3)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7109ee3449164ef6b5f238553cf7f8f9
Source dataset
uspto-grants-2004_09
Patent number
US06790850B1

Reaction notes

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