Dimethylformamide → Methyl 3-formyl-2-(4-nitrobenzyloxy)benzoate

HRID 1761925Notes

Reaction equation

HRID 1761925 reaction equation
[CH:1]([C:3]1[C:4]([OH:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2].[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:1]([C:3]1[C:4]([O:13][CH2:21][C:20]2[CH:23]=[CH:24][C:17]([N+:14]([O-:16])=[O:15])=[CH:18][CH:19]=2)=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 345559Methyl 3-formyl-2-hydroxybenzoate

Product 1

HCID 20043641Methyl 3-formyl-2-(4-nitrobenzyloxy)benzoateYield 99.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of methyl 3-formyl-2-hydroxybenzoate, 11.7 g of 4-nitrobenzyl bromide, 11.7 g of potassium carbonate and 70 ml of dimethylformamide is stirred at room temperature for 1 hour. The reaction mixture is poured into water and the aqueous mixture is extracted with ethyl acetate. The extract is dried and evaporated to remove solvent to give 8.70 g of methyl 3-formyl-2-(4-nitrobenzyloxy)benzoate as colorless powder.

Workup

  1. extractionthe aqueous mixture is extracted with ethyl acetate
  2. customThe extract is dried
  3. customevaporated
  4. customto remove solvent

Sources & evidence

ORD record
ord-7b9e0f0d8a6743c392008a68cad4bc78
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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