Water → Ethyl 4-(4-methoxystyryl)benzoate

HRID 262199Notes

Reaction equation

HRID 262199 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH:7]=[CH:8][C:9]2[C:10](C#N)=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[OH2:19]>Cl.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:8][C:9]2[CH:14]=[CH:13][C:12]([C:1]([O:2][CH2:3][CH3:4])=[O:19])=[CH:11][CH:10]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 962WaterHCID 543107412-[2-(4-Methoxyphenyl)ethenyl]benzonitrile

Product 1

HCID 53892329Ethyl 4-(4-methoxystyryl)benzoate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent3×HCID 702EthanolSolvent3×

Procedure

4'-Methoxystilbenenitrile, 72.5 g. [Neher et al., Helv. Chim. Acta 29, 449-67 (1946)] in 1 liter of 5N hydrogen chloride in ethanol was heated under reflux for eight hours. An additional 100 ml. of 10N hydrogen chloride in ethanol was added and refluxing continued for about sixteen hours. An additional 100 ml. of 10N hydrogen chloride in ethanol was then added and refluxing continued for six hours. The reaction mixture was diluted with 2 liters of water, and the solid product which separated was collected by filtration and air-dried. The product was dissolved in methylene dichloride, dried over anhydrous magnesium sulfate and the solvent removed to give 73 g. of ethyl 4-(4-methoxystyryl)benzoate, m.p. 191°-192° C. when recrystallized from ethanol.

Workup

  1. temperatureunder reflux for eight hours
  2. temperaturerefluxing
  3. waitcontinued for about sixteen hours
  4. temperaturerefluxing
  5. customthe solid product which separated
  6. filtrationwas collected by filtration
  7. customair-dried
  8. dissolutionThe product was dissolved in methylene dichloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent removed
  11. customto give 73 g
  12. customof ethyl 4-(4-methoxystyryl)benzoate, m.p. 191°-192° C. when recrystallized from ethanol

Sources & evidence

ORD record
ord-060075733f7a43b2b90f682aed3591a4
Source dataset
uspto-grants-1979_05
Patent number
US04153719

Reaction notes

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