Water → Dimethyl bis(4-nitrobenzyl)malonate

HRID 2246019Notes

Reaction equation

HRID 2246019 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].[OH2:23]>O1CCCC1>[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19][C:2]([CH2:19][C:18]2[CH:21]=[CH:22][C:15]([N+:12]([O-:13])=[O:23])=[CH:16][CH:17]=2)([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:17][CH:16]=1)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromide

Product 1

HCID 59217458Dimethyl bis(4-nitrobenzyl)malonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

16.25 g (0.123 mol) of dimethyl malonate were dissolved in 500 ml tetrahydrofurane. A suspension of 10.74 g (0.246 mol) sodium hydride 55% dispersion in mineral oil and 20 ml tetrahydrofurane were added at 0° C. in 1 h. After 0.5 h, a mixture of 53.2 g (0.246 mol) 4-nitrobenzyl bromide and 200 ml tetrahydrofurane was added dropwise. After 18.5 h at room temperature, the reaction mixture was added to water. The product was collected by filtration and washed with a lot of water to yield 52.8 g of dimethyl bis(4-nitrobenzyl)malonate as yellowish powder. The product was used without further purification.

Workup

  1. additionwere added at 0° C. in 1 h
  2. additionwas added dropwise
  3. waitAfter 18.5 h at room temperature
  4. filtrationThe product was collected by filtration
  5. washwashed with a lot of water

Sources & evidence

ORD record
ord-7bca0b26d2704e86853c8a2013168430
Source dataset
uspto-grants-2010_03
Patent number
US07687118B2

Reaction notes

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