Potassium Hydroxide → Ethyl 2-benzylacrylate

HRID 478030Notes

Reaction equation

HRID 478030 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-benzylacrylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4.0 g of KOH in 50 ml of ethanol are added at room temperature to 20 g of benzylmalonic acid diethyl ester in 40 ml of ethanol and the whole is stirred overnight at room temperature, concentrated by evaporation, 7.1 ml of water are added and the whole is acidified in an ice bath with 6.3 ml of concentrated hydrochloric acid. Partitioning between water and ether is carried out, and the organic phase is dried and the ether is distilled off. 12.9 ml of pyridine, 0.61 g of piperidine and 1.78 g of paraformaldehyde are added to the residue. The mixture is heated in an oil bath (130°) for 90 minutes, cooled, 220 ml of water are added and extraction is carried out 3 times with 75 ml of n-hexane. The combined organic phases are washed with water, 1N HCl, water, saturated NaHCO3 solution and brine. The title compound is obtained by distillation. 1H-NMR (DMSO-d6): 1.2 ppm (t, 3 H); 3.6 (d, 2H); 4.1 (q, 2H); 5.6 (m, 1H); 6.15 (m, 1H); 7.25 (m, 5H).

Workup

  1. concentrationconcentrated by evaporation, 7.1 ml of water
  2. additionare added
  3. customthe whole is acidified in an ice bath with 6.3 ml of concentrated hydrochloric acid
  4. customPartitioning between water and ether
  5. customthe organic phase is dried
  6. distillationthe ether is distilled off
  7. addition12.9 ml of pyridine, 0.61 g of piperidine and 1.78 g of paraformaldehyde are added to the residue
  8. temperatureThe mixture is heated in an oil bath (130°) for 90 minutes
  9. temperaturecooled
  10. addition220 ml of water are added
  11. extractionextraction
  12. washThe combined organic phases are washed with water, 1N HCl, water, saturated NaHCO3 solution and brine

Sources & evidence

ORD record
ord-fb385ac51514452c8c08291453c3af44
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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