Phenylacetaldehyde → HCID 53782451, compound

HRID 1981344Notes

Reaction equation

HRID 1981344 reaction equation
C1(C)C=C[C:4]([S:7](O)(=O)=O)=[CH:3][CH:2]=1.C1CCCCC1.[CH2:18]([SH:21])[CH2:19][CH3:20].[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:18]([S:21][CH:29]([S:7][CH2:4][CH2:3][CH3:2])[CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 998PhenylacetaldehydeHCID 6101p-Toluenesulfonic acidHCID 7848Propyl mercaptanHCID 8078Cyclohexane

Product 1

HCID 53782451HCID 53782451, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml reaction flask equipped with thermometer, 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 7.6 grams (0.1 mole) of n-propyl mercaptan. With stirring over a period of 25 minutes, 6 grams (0.05 moles) of phenyl acetaldehyde is added to the reaction mass. The reaction mass is then heated to reflux and refluxed for a period of 8.5 hours. During the refluxing period, water of reaction is removed. At the end of the refluxing 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 then dried over anhydrous sodium sulfate and filtered. The filtrate is distilled on a Microvigreux column yielding the following five fractions:

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped with thermometer
  3. temperaturereflux condenser and magnetic stirring bar
  4. customhot plate equipped with magnetic stirring apparatus
  5. temperatureThe reaction mass is then heated
  6. temperatureto reflux
  7. temperaturerefluxed for a period of 8.5 hours
  8. customis removed
  9. customtransferred to a separatory funnel
  10. washThe reaction mass is washed with one 50 ml portion of saturated aqueous sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. distillationThe filtrate is distilled on a Microvigreux column
  14. customyielding the following five fractions

Sources & evidence

ORD record
ord-ac3a83d51356460fbe4b5fa5b118b6bd
Source dataset
uspto-grants-1985_04
Patent number
US04514429

Reaction notes

Loading…