Phenylacetaldehyde → 2-Benzyl-4,5-Dimethyl-1,3-Dithiolane

HRID 462571

Reaction equation

HRID 462571 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1.[CH3:18][CH:19]([SH:23])[CH:20]([SH:22])[CH3:21].[C:24]1([CH2:30][CH:31]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[CH2:30]([CH:31]1[S:23][CH:19]([CH3:18])[CH:20]([CH3:21])[S:22]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 6101p-Toluenesulfonic acidHCID 8078CyclohexaneHCID 5483532,3-Butanedithiol

Product 1

HCID 203986752-Benzyl-4,5-Dimethyl-1,3-Dithiolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml flask equipped with reflux condenser and magnetic stirring bar and hot plate equipped with magnetic stirring apparatus is placed 0.2 grams of para-toluenesulfonic acid, 5 ml cyclohexane and 6.1 grams (0.05 moles) of 2,3-butanedithiol. With stirring, over a period of 30 minutes, 6.0 grams (0.05 moles) of phenylacetaldehyde is added to the reaction mass. The reaction mass is then heated to reflux and refluxed for a period of 10 hours during which time water of formation is removed. After the 10 hour period, the reaction mass is cooled and transferred to a separatory funnel. The reaction mass is washed with one 50 ml portion of saturated sodium chloride, dried over anhydrous sodium sulfate and filtered. The resulting filtrate is then distilled on a Microvigreux column yielding the following four fractions:

Workup

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

Sources & evidence

ORD record
ord-be3009770ae34e7aa9fa1040ba40f2e6
Source dataset
uspto-grants-1985_05
Patent number
US04515968

Linked notes

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