Potassium Carbonate → Methyl (4-formyl-2-methoxy-3-nitrophenoxy)acetate

HRID 1821432Notes

Reaction equation

HRID 1821432 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[C:3]([O:13][CH3:14])[C:4]=1[N+:10]([O-:12])=[O:11])=[O:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

Product 1

HCID 86628221Methyl (4-formyl-2-methoxy-3-nitrophenoxy)acetateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-3-methoxy-2-nitrobenzaldehyde (2.0 g, 10 mmol) in DMF (10 mL) was added with methyl bromoacetate (1.1 mL, 11 mmol) and potassium carbonate (2.1 g, 15 mmol), followed by stirring for 1.5 hours. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to obtain methyl (4-formyl-2-methoxy-3-nitrophenoxy)acetate (2.2 g, 84%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-75b5dd46d1a94d4da39fbfbfbe008008
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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