Diethyl Malonate → HCID 23106803, compound

HRID 2376658Notes

Reaction equation

HRID 2376658 reaction equation
C([O:3][C:4](=[O:23])[CH:5]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21])C(OCC)=O)C.C(OCC)(=O)CC(OCC)=O>Cl.O1CCOCC1>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:5][C:4]([OH:23])=[O:3])=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 7761Diethyl MalonateHCID 59855772HCID 59855772, compound

Product 1

HCID 23106803HCID 23106803, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of diethyl(4-acetyl-2-nitrophenyl)malonate and diethyl malonate (54.1 g) prepared by step a) was dissolved in 4M HCl (800 mL)/dioxane (800 mL), and the solution was stirred at 100° C. for 8 hours. After cooling, dioxane was removed in vacuo, and the aqueous layer was extracted with chloroform (200 mL×1, 100 mL×2). The organic layers were combined, dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the object compound (23.1 g, quantitatively) as a brown solid.

Workup

  1. temperatureAfter cooling
  2. customdioxane was removed in vacuo
  3. extractionthe aqueous layer was extracted with chloroform (200 mL×1, 100 mL×2)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customto give the object compound (23.1 g

Sources & evidence

ORD record
ord-2bdc33aa10e94bb69ef643ed7f5a8b30
Source dataset
uspto-grants-2008_12
Patent number
US07468364B2

Reaction notes

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