Diethyl Oxalate → Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoate

HRID 1748241Notes

Reaction equation

HRID 1748241 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([O:18][C:19](=[O:25])[C:20](OCC)=[O:21])[CH3:17].[O-]CC.[Na+]>C(O)C>[CH2:16]([O:18][C:19](=[O:25])[C:20](=[O:21])[CH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])[CH3:17]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 14945864Ethyl 4-methyl-3-nitrobenzoate

Product 1

HCID 58767563Ethyl 4-(3-ethoxy-2,3-dioxopropyl)-3-nitrobenzoateYield 77.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-methyl-3-nitrobenzoate (80 g, 0.38 mol) and oxalic acid diethyl ester (57 mL, 0.42 mol) in ethanol (1000 mL) is added sodium ethoxide (430 mL, 1.15 mol, 21% in ethanol). The resulting brown solution is stirred at room temperature for 16 h. The reaction is quenched with 3N HCl to neutral pH and diluted with water (2000 mL). The resulting white precipitate is filtered and dried in vacuum to afford the title compound (91 g, 77%).

Workup

  1. customThe reaction is quenched with 3N HCl to neutral pH
  2. additiondiluted with water (2000 mL)
  3. filtrationThe resulting white precipitate is filtered
  4. customdried in vacuum

Sources & evidence

ORD record
ord-06eaffc7111d475cbd130299e6ebe52c
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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