Potassium Hydroxide → Ethyl 2-benzylacrylate

HRID 1034446Notes

Reaction equation

HRID 1034446 reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6](=[O:20])[CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8](OCC)=O)[CH3:4]>C(O)C>[CH2:3]([O:5][C:6](=[O:20])[C:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:8])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 11084648Ethyl 2-benzylacrylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 8.5 g of KOH in 100 ml of ethanol was added at room temperature to 40 g of benzylmalonic acid diethyl ester in 80 ml of ethanol. The mixture was stirred overnight at room temperature, then concentrated by evaporation, thereafter 14 ml of water was added and then the mixture was acidified in an ice bath with 12.6 ml of concentrated hydrochloric acid. Partitioning between water and ether was carried out, the organic phase was dried and the ether was distilled off. Then, 26 ml of pyridine, 1.22 g of piperidine and 3.56 g of paraformaldehyde were added to the residue. The mixture was heated in an oil bath (130°) for 90 minutes, cooled, 440 ml of water was added and extraction was carried out 3 times with 150 ml of n-hexane. The combined organic phases were washed alternatively with water, 1N HCl, water, saturated NaHCO3 solution and brine. The solution was dried (MgSO4) and evaporated to give the title compound as colorless oil (26 g, 85% yield)

Workup

  1. concentrationconcentrated by evaporation
  2. addition14 ml of water was added
  3. customthe mixture was acidified in an ice bath with 12.6 ml of concentrated hydrochloric acid
  4. customPartitioning between water and ether
  5. customthe organic phase was dried
  6. distillationthe ether was distilled off
  7. additionThen, 26 ml of pyridine, 1.22 g of piperidine and 3.56 g of paraformaldehyde were added to the residue
  8. temperatureThe mixture was heated in an oil bath (130°) for 90 minutes
  9. temperaturecooled
  10. addition440 ml of water was added
  11. extractionextraction
  12. washThe combined organic phases were washed alternatively with water, 1N HCl, water, saturated NaHCO3 solution and brine
  13. dry with materialThe solution was dried (MgSO4)
  14. customevaporated

Sources & evidence

ORD record
ord-8e3f69d8b8164e6baaab9452fe63ab01
Source dataset
uspto-grants-1994_05
Patent number
US05317039

Reaction notes

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