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

HRID 1882193Notes

Reaction equation

HRID 1882193 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-6a32dee5ef44436790fb1950b2a24132
Source dataset
uspto-grants-2012_11
Patent number
US08318952B2

Reaction notes

Loading…