Diethyl Malonate → Malonic acid, piperonyl-, diethyl ester

HRID 2188326Notes

Reaction equation

HRID 2188326 reaction equation
[O-]CC.[Na+].[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:16]1[O:24][C:23]2[CH:22]=[CH:21][C:20]([CH2:25]Cl)=[CH:19][C:18]=2[O:17]1>C(O)C>[CH2:14]([O:13][C:5](=[O:12])[CH:6]([CH2:25][C:20]1[CH:21]=[CH:22][C:23]2[O:24][CH2:16][O:17][C:18]=2[CH:19]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:15]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 2723922Sodium ethoxide

Product 1

HCID 140890Malonic acid, piperonyl-, diethyl esterYield 87.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

60.17 g of sodium ethoxide were dissolved in 1127 ml of ethanol. To this solution, 336.4 g of diethyl malonate and 119.42 g of [(3,4-methylendioxy)phenyl]methyl chloride were added and the mixture was refluxed for 3 hours. After the reaction was completed, the solvent was removed under reduced pressure and water was added to the residue. After extraction with ethyl acetate, the ethyl acetate was dried with sodium sulfate anhydride. After removing the solvent under reduced pressure and purification with distillation, 181.1 g of 2-[[(3,4-methylenedioxy)phenyl]methyl]malonic acid diethyl ester were obtained.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customthe solvent was removed under reduced pressure and water
  3. additionwas added to the residue
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialthe ethyl acetate was dried with sodium sulfate anhydride
  6. customAfter removing the solvent
  7. customunder reduced pressure and purification
  8. distillationwith distillation

Sources & evidence

ORD record
ord-7e3d80f9abdd4a7b87b1f7a99856a3a4
Source dataset
uspto-grants-2002_06
Patent number
US06410773B1

Reaction notes

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