Diethyl Malonate → Diethyl (3-methyl-4-nitrobenzyl)malonate

HRID 1451639Notes

Reaction equation

HRID 1451639 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[CH2:16]Br>C([O-])C.[Na+]>[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[CH2:16][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 44459783-Methyl-4-nitrobenzyl bromide

Product 1

HCID 54253538Diethyl (3-methyl-4-nitrobenzyl)malonate

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

To a solution of sodium ethanolate [prepared from 1.35 g Na in ethanol (30 ml)] were added diethyl malonate (9.2 ml) and then dropwise 3-methyl-4-nitrobenzyl bromide (13.4 g). The mixture was stirred 30 minutes at room temperature, then 30 minutes under reflux and then concentrated. The residue is treated with water and hexane, the precipitate filtered and the filtrate extracted with diethyl ether. The organic extract was dried on sodium sulfate and concentrate to give the title compound as an oil (4 g).

Workup

  1. temperature30 minutes under reflux
  2. concentrationconcentrated
  3. additionThe residue is treated with water and hexane
  4. filtrationthe precipitate filtered
  5. extractionthe filtrate extracted with diethyl ether
  6. extractionThe organic extract
  7. customwas dried on sodium sulfate
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-78659a571efd4bcf9572276fb9e0cf58
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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