5-Nitro-2-(phenylsulfanyl)benzaldehyde → [5-Nitro-2-(phenylsulfanyl)phenyl]methanol

HRID 435616Notes

Reaction equation

HRID 435616 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].[BH4-].[Na+]>C(O)C.O>[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:11]=1)[CH2:7][OH:8])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 29810675-Nitro-2-(phenylsulfanyl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 54372723[5-Nitro-2-(phenylsulfanyl)phenyl]methanol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

450 g of 3-nitro-6-(phenylthio)-benzaldehyde are suspended in 4 litres of ethanol and treated portionwise with 111 g of sodium borohydride. The mixture is stirred for a further 6 hours. The mixture is then diluted with 4 litres of water and extracted with ether. The organic solution is washed successively with water and aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated under reduced pressure. The crude product is recrystallised from benzene/petroleum ether. There is obtained 3-nitro-6-(phenylthio)-benzyl alcohol of melting point 104°-107° C.

Workup

  1. extractionextracted with ether
  2. washThe organic solution is washed successively with water and aqueous sodium bicarbonate solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude product is recrystallised from benzene/petroleum ether

Sources & evidence

ORD record
ord-4b8c419171db43af8d23c23e884b0e6e
Source dataset
uspto-grants-1977_02
Patent number
US04006145

Reaction notes

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