Potassium Carbonate → 2-[(4-Methoxybenzyl)oxy]-3-nitrobenzaldehyde

HRID 2357763Notes

Reaction equation

HRID 2357763 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>CN(C)C=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:1][C:2]2[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 789342-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 231246412-[(4-Methoxybenzyl)oxy]-3-nitrobenzaldehydeYield 80.9%

Reagents, catalysts & solvents 2

HCID 2724141Tetrabutylammonium FluorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxy-3-nitrobenzaldehyde (3 g) in dimethylformamide (20 mL) were sequentially added potassium carbonate (3.72 g), tetra-n-butylammonium fluoride (331 mg) and 1-(chloromethyl)-4-methoxybenzene (3.37 g), and the mixture was stirred for 11 hours at room temperature. The reaction mixture was poured into ice-water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was washed with tert-butyl methyl ether to give the title compound (4.17 g) having the following physical data.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with tert-butyl methyl ether

Sources & evidence

ORD record
ord-0d472cb046214f0ab2787ddb3d6495f1
Source dataset
uspto-grants-2010_07
Patent number
US07763610B2

Reaction notes

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