Benzaldehyde → 2-(Methylsulanylmethyl)-3-phenylprop-2-enal

HRID 461923Notes

Reaction equation

HRID 461923 reaction equation
[OH-].[K+].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][S:12][CH2:13][CH2:14][CH:15]=[O:16]>CO>[CH3:11][S:12][CH2:13][C:14](=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14797Potassium HydroxideHCID 18635Methional

Product 1

HCID 533951952-(Methylsulanylmethyl)-3-phenylprop-2-enalYield 33.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 100 ml three necked reaction flask equipped with stirrer, thermometer and addition funnel is charged a solution of 0.5 grams of potassium hydroxide in 10 ml methanol. Benzaldehyde (10.0 grams) is added as the mixture is cooled to 5°-10° C. Methional (10.0 grams) is then added dropwise while maintaining the reaction temperature at 5°-10° C. The mixture is then allowed to warm to room temperature and stirred for a period of 1 hour. Most of the solvent is evaporated at reduced pressure and the mixture is partitioned between water and ether. The organic layer is washed several times with water and once with saturated brine. The solvent is evaporated leaving a yellow oil which is distilled to give 6.1 grams product, boiling point 104°-111° C (0.4 mm Hg).

Workup

  1. additionthermometer and addition funnel
  2. temperatureis cooled to 5°-10° C
  3. temperaturewhile maintaining the reaction temperature at 5°-10° C
  4. customMost of the solvent is evaporated at reduced pressure
  5. customthe mixture is partitioned between water and ether
  6. washThe organic layer is washed several times with water
  7. customThe solvent is evaporated
  8. customleaving a yellow oil which
  9. distillationis distilled

Sources & evidence

ORD record
ord-bc77cc24073348cfa751cfc93f715102
Source dataset
uspto-grants-1977_12
Patent number
US04064279

Reaction notes

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