p-Toluenesulfonic acid → 2-[Bis(propylsulfanyl)methyl]furan

HRID 462576Notes

Reaction equation

HRID 462576 reaction equation
C1(C)C=C[C:4]([S:7](O)(=O)=O)=[CH:3][CH:2]=1.[CH2:12]([SH:15])[CH2:13][CH3:14].[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=O>C1CCCCC1>[CH2:12]([S:15][CH:21]([S:7][CH2:4][CH2:3][CH3:2])[C:17]1[O:16][CH:20]=[CH:19][CH:18]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7362FurfuralHCID 7848Propyl mercaptan

Product 1

HCID 543946512-[Bis(propylsulfanyl)methyl]furan

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Into a 100 ml reaction flask equipped with reflux condenser, thermometer and magnetic stirring bar with hot plate and magnetic stirring apparatus is placed 0.5 grams of para-toluenesulfonic acid, 5 ml cyclohexane and 15.2 grams (0.2 moles) of n-propyl mercaptan. Over a period of 25 minutes, 9.6 grams (0.1 mole) of 2-furaldehyde is added with stirring. The reaction mixture is then heated to reflux and refluxed for a period of 10 hours while removing water of reaction. The the end of the 10 hour reflux period, the reaction mass is cooled to room temperature and transferred to a separatory funnel. The reaction mass is washed with one 50 ml portion of saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate and filtered. The resulting filtrate is then distilled on a Microvigreux column yielding the following fractions:

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped
  3. temperaturewith reflux condenser
  4. customthermometer and magnetic stirring bar with hot plate and magnetic stirring apparatus is placed
  5. temperatureThe reaction mixture is then heated
  6. temperatureto reflux
  7. temperaturerefluxed for a period of 10 hours
  8. customwhile removing
  9. customwater of reaction
  10. temperatureThe the end of the 10 hour reflux period
  11. customtransferred to a separatory funnel
  12. washThe reaction mass is washed with one 50 ml portion of saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. distillationThe resulting filtrate is then distilled on a Microvigreux column
  16. customyielding the following fractions

Sources & evidence

ORD record
ord-51c1370fda02433bab97dd0aabc43635
Source dataset
uspto-grants-1985_05
Patent number
US04515968

Reaction notes

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