2-(Methylthio)benzaldehyde → (2-Methylsulfanylphenyl)methanol

HRID 1364568Notes

Reaction equation

HRID 1364568 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+]>C(O)C.O>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][OH:6]

Participants

5

Reactant 2

HCID 2864432-(Methylthio)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 3551404(2-Methylsulfanylphenyl)methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1.00 g (6.57 mmol) of 2-methylsulfanylbenzaldehyde in 10 mL of ethanol at 0° C. was added 250 mg of NaBH4. The reaction was stirred at 0° C. for 10 min, then diluted with 50 mL of water. The aqueous suspension was extracted with diethyl ether (3×15 mL), then the combined ether layers were back extracted with brine (1×10 mL), dried over MgSO4, filtered, and concentrated in vacuo to 1.01 g (100%) of the titled compound as an oil.

Workup

  1. extractionThe aqueous suspension was extracted with diethyl ether (3×15 mL)
  2. extractionthe combined ether layers were back extracted with brine (1×10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to 1.01 g (100%) of the titled compound as an oil

Sources & evidence

ORD record
ord-e1a89bee1a054225ad2748a0bb28602c
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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