Hydrochloric Acid → Diethyl 2-(4-methoxyphenyl)malonate

HRID 361890

Reaction equation

HRID 361890 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1.[C:15](=O)([O:19]CC)[O:16][CH2:17][CH3:18].[H-].[Na+].Cl>CN(C)C=O>[CH2:13]([O:12][C:10]([CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:15]([O:16][CH2:17][CH3:18])=[O:19])=[O:11])[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 84174Ethyl 4-methoxyphenylacetate

Product 1

HCID 2785178Diethyl 2-(4-methoxyphenyl)malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

27.7 g of ethyl 4-methoxyphenylacetate and 34 ml of diethyl carbonate were dissolved in 150 ml of N,N-dimethylformamide, and the solution was subjected to reflux under heating, while gradually adding 6.5 g of sodium hydride for 1 hour. After further refluxing under heating for 2 hours, the resulting reaction solution was poured into a mixture of ice water and hydrochloric acid, followed by extraction with ethyl acetate. The resulting organic layer was washed with water, and then dried to distill off the solvent. The residue thus obtained was purified by silica gel column chromatography using toluene as an eluant, thereby obtaining 26.7 g of ethyl 2-ethoxycarbonyl-2-(4-methoxyphenyl)acetate in the form of light yellow oil.

Workup

  1. temperatureto reflux
  2. temperatureunder heating
  3. temperatureAfter further refluxing
  4. temperatureunder heating for 2 hours
  5. customthe resulting reaction solution
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resulting organic layer was washed with water
  8. customdried
  9. distillationto distill off the solvent
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c730059c8a343e68e04bb4b9cc7b260
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Linked notes

Loading…