Reaction #65383

Reaction equation

2-nitro-4-trifluoromethylphenol

calcium carbonate

2-bromoisobutyraldehyde

→

2-(2-nitro-4-trifluoromethylphenoxy)isobutyraldehyde

Yield 33.1%

Solvents

N,N-dimethylformamide

N,N-dimethylformamide

—

ice water

Conditions

Workup

1. 1
   Extractionextracted with toluene
2. 2
   WashThe organic layer was washed with 0.5 N aqueous sodium hydroxide solution and water in that order
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   OtherThe residue was chromatographed on a silica gel column and elution
6. 6
   OtherThe Crystals from the eluate were recrystallized from 15 ml of hexane twice

Procedure

To a mixture of 10 g of 2-nitro-4-trifluoromethylphenol, 8.0 g of anhydrous calcium carbonate and 30 ml of N,N-dimethylformamide was added dropwise a solution of 8.8 g of 2-bromoisobutyraldehyde in 23 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 4 days. The reaction mixture was then poured in ice-water and extracted with toluene. The organic layer was washed with 0.5 N aqueous sodium hydroxide solution and water in that order and dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was chromatographed on a silica gel column and elution was carried out with hexane-ethyl acetate (3:1). The Crystals from the eluate were recrystallized from 15 ml of hexane twice to give 4.428 g of 2-(2-nitro-4-trifluoromethylphenoxy)isobutyraldehyde.

Source