4-Nitrobenzaldehyde → 4-(Butylsulfanyl)benzaldehyde

HRID 1583884Notes

Reaction equation

HRID 1583884 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH3:18][CH2:19][CH2:20][CH2:21][SH:22].CN(C)C=O>O>[CH2:21]([S:22][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)[CH2:20][CH2:19][CH3:18]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 6228DimethylformamideHCID 8012ButanethiolHCID 11430Potassium Carbonate

Product 1

HCID 202571664-(Butylsulfanyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-nitrobenzaldehyde (10.0 g), potassium carbonate (10.0 g), n-butylthiol (12.5 ml) and dimethylformamide (12.5 ml) was heated at 100° C. for a period of 16 hours, cooled and poured into water (250 ml). The aqueous mixture was extracted with diethyl ether (4×250 ml) and the combined organic phases were washed with aqueous 2% sodium hydroxide solution (5×100 ml) and finally with water. The organic phase was dried over anhydrous sodium sulfate and the solvent was removed by distillation to give 4-(n-butylthio)benzaldehyde (10.8 g) as a reddish coloured oil. The product was characterized by proton nuclear magnetic resonance spectroscopy. Pmr (CDCl3 ; δ in ppm): 0.97 (3H, t); 1.60 (4H, m); 3.03 (2H, t); 7.32 (2H, d); 7.77 (2H, d); 9.89 (1H, s).

Workup

  1. temperaturecooled
  2. extractionThe aqueous mixture was extracted with diethyl ether (4×250 ml)
  3. washthe combined organic phases were washed with aqueous 2% sodium hydroxide solution (5×100 ml) and finally with water
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-278393bbb1c645e7acd109e43f85de04
Source dataset
uspto-grants-1985_11
Patent number
US04555263

Reaction notes

Loading…