Ethanol → Diethyl 2-nitro-4-benzoylphenylmalonate

HRID 414411Notes

Reaction equation

HRID 414411 reaction equation
[Na].C(O)C.[C:5]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl[C:17]1[CH:30]=[CH:29][C:20]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])=[CH:19][C:18]=1[N+:31]([O-:33])=[O:32]>C(Cl)Cl>[N+:31]([C:18]1[CH:19]=[C:20]([C:21](=[O:22])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:29]=[CH:30][C:17]=1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]([O:13][CH2:14][CH3:15])=[O:12])([O-:33])=[O:32]

Participants

6

Reactant 4

HCID 702EthanolHCID 7761Diethyl MalonateHCID 417434-Chloro-3-nitrobenzophenoneHCID 5360545Sodium

Product 1

HCID 13408230Diethyl 2-nitro-4-benzoylphenylmalonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of sodium ethoxide, formed by reacting 4.6 g. (0.2 mole) of sodium metal with 200 ml. of ethanol, at 0° C. was added 32 g. (0.2 mole) of diethyl malonate followed by 26.1 g. (0.1 mole) of 4-chloro-3-nitrobenzophenone. The mixture was allowed to stir at room temperature for 2 hours and was then poured into 400 ml. of ice cold 2N hydrochloric acid and 300 ml. of methylene chloride. The organic layer was separated, dried over magnesium sulfate and concentrated to an oil. The residual oil was induced to crystallize by trituration with hexane containing trace amounts of diisopropyl ether, 34.75 g., m.p. 68°-70° C. The sample was further purified by trituration with hot hexane-diisopropyl ether, 30.84 g. (80% yield). Anal. Calcd. for C20H19NO7 : C, 62.3; H, 5.0; N, 3.6. Found: C, 62.3; H, 4.9; N, 3.6.

Workup

  1. additionwas then poured into 400 ml
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to an oil
  5. customto crystallize by trituration with hexane containing trace amounts of diisopropyl ether, 34.75 g
  6. customThe sample was further purified by trituration with hot hexane-diisopropyl ether, 30.84 g

Sources & evidence

ORD record
ord-9542ca7049e848a895849268ec9699ae
Source dataset
uspto-grants-1988_12
Patent number
US04791129

Reaction notes

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