Hydrochloric Acid → HCID 54118611, compound

HRID 2256931Notes

Reaction equation

HRID 2256931 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[N+:13]([C:16]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19])([O-:15])=[O:14].Cl>C(O)C.C(OCC)C.C(Cl)(Cl)(Cl)Cl>[N+:13]([C:16]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:17]=1[C:18]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:19])([O-:15])=[O:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 54118611HCID 54118611, compoundYield 96.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent4×HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of magnesium turnings (4.94 g) and carbon tetrachloride (2 ml) in ethanol (35 ml) was warmed to 50° C. until the reaction started. Diethyl ether (150 ml) was then added cautiously, with stirring. A solution of diethyl malonate (32.5 g) in diethyl ether (50 ml) was then added dropwise, then stirred and heated at reflux for 2 hours. After cooling the mixture, diethyl ether (150 ml) was added. A solution of 2-nitro-4-trifluoromethylbenzoyl chloride (50.7 g) in diethyl ether (100 ml) was added dropwise. The mixture was heated at reflux for 2 hours. After cooling, hydrochloric acid (2M,200 ml) was added and the layers were separated. The organic layer was washed with water, dried (anhydrous sodium sulphate), and filtered. The filtrate was evaporated to dryness, to give diethyl 2-nitro-4-trifluoromethylbenzoylmalonate (72.6 g), in the form of an off-white solid, m.p. 60° C.

Workup

  1. stirringstirred
  2. temperatureheated
  3. temperatureat reflux for 2 hours
  4. additionwas added
  5. temperatureThe mixture was heated
  6. temperatureat reflux for 2 hours
  7. temperatureAfter cooling
  8. customthe layers were separated
  9. washThe organic layer was washed with water
  10. dry with materialdried (anhydrous sodium sulphate)
  11. filtrationfiltered
  12. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-bbcaa34655e54b4596297f08de102c7e
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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