Benzaldehyde → [Bis(propylsulfanyl)methyl]benzene

HRID 462572Notes

Reaction equation

HRID 462572 reaction equation
C1CCCCC1.C1(C)C=C[C:10]([S:13](O)(=O)=O)=[CH:9][CH:8]=1.[CH2:18]([SH:21])[CH2:19][CH3:20].[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:18]([S:21][CH:22]([S:13][CH2:10][CH2:9][CH3:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 7848Propyl mercaptanHCID 8078Cyclohexane

Product 1

HCID 11345484[Bis(propylsulfanyl)methyl]benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 cc reaction flask equipped with reflux condenser, magnetic stirring bar, and hot plate equipped with magnetic stirring apparatus is placed 10 ml cyclohexane, 0.5 grams of para-toluenesulfonic acid and 15.2 grams (0.2 moles) of n-propyl mercaptan. Over a period of 25 minutes with stirring is added 10.6 grams (0.1 moles) of benzaldehyde. The reaction mass is heated to reflux with stirring and refluxed for a period of 7 hours. During the refluxing, water of reaction is removed. At the end of the 7 hour period, the reaction mass is cooled to room temperature and transferred to a separatory funnel. The reaction mass is then washed with one 50 ml portion of a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate and filtered. The resulting filtrate is distilled on a Microvigreux column yielding the following five fractions:

Workup

  1. customInto a 100 cc reaction flask
  2. customequipped
  3. temperaturewith reflux condenser, magnetic stirring bar
  4. customhot plate equipped with magnetic stirring apparatus
  5. temperatureThe reaction mass is heated
  6. temperatureto reflux
  7. stirringwith stirring
  8. temperaturerefluxed for a period of 7 hours
  9. customis removed
  10. customtransferred to a separatory funnel
  11. washThe reaction mass is then washed with one 50 ml portion of a saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfiltered
  14. distillationThe resulting filtrate is distilled on a Microvigreux column
  15. customyielding the following five fractions

Sources & evidence

ORD record
ord-d94050edf8f24c139559c40c4de62551
Source dataset
uspto-grants-1985_05
Patent number
US04515968

Reaction notes

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