Potassium Hydroxide → Ethyl alpha-(phenethyl)acrylate

HRID 462432Notes

Reaction equation

HRID 462432 reaction equation
[CH2:1]([CH:9]([C:15](OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[K+]>C(O)C>[CH2:15]=[C:9]([CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 811191,3-Diethyl 2-(2-phenylethyl)propanedioate

Product 1

HCID 11117162Ethyl alpha-(phenethyl)acrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

26.6 g (0.1 mole) of diethyl phenethylmalonate were added dropwise in the course of an hour, with stirring, to 5.6 g of KOH in 65 ml of absolute ethanol, the mixture was stirred at room temperature for 15 hours and then boiled for 5 minutes. The ethanol was removed in vacuo, ice-water was added and the mixture was extracted with ether. The aqueous phase was acidified with 2N hydrochloric acid and extracted with ether. The second extract was dried and evaporated and then neutralized with 8.8 ml of diethylamine. 12 ml of 30% strength formaldehyde solution were added, the mixture was stirred for 3 hours, then saturated with potassium carbonate, extracted with ether, the extract was washed with dilute hydrochloric acid, dried and evaporated.

Workup

  1. waitboiled for 5 minutes
  2. customThe ethanol was removed in vacuo, ice-water
  3. additionwas added
  4. extractionthe mixture was extracted with ether
  5. extractionextracted with ether
  6. extractionThe second extract
  7. customwas dried
  8. customevaporated
  9. addition12 ml of 30% strength formaldehyde solution were added
  10. stirringthe mixture was stirred for 3 hours
  11. extractionsaturated with potassium carbonate, extracted with ether
  12. washthe extract was washed with dilute hydrochloric acid
  13. customdried
  14. customevaporated

Sources & evidence

ORD record
ord-87b63fa108da452caa07dffe641dc131
Source dataset
uspto-grants-1985_05
Patent number
US04515803

Reaction notes

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