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

HRID 1097358Notes

Reaction equation

HRID 1097358 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 subtitle 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-0cdd2c7fbed5402c931c255b269ab1be
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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