Reaction #3028

Reaction equation

hydrochloric acid

2,4-dinitrophenol

octadecyl bromide

sodium carbonate

→

1-octadecyloxy-2,4-dinitrobenzene

Yield 79.1%

Solvents

dimethylformamide

water

Conditions

Workup

1. 1
   Extractionextracted with ether
2. 2
   WashThe extracts were washed with water and brine
3. 3
   Dryingdried over magnesium sulfate
4. 4
   OtherThe solvent was removed
5. 5
   Otherthe solid recrystallized

Procedure

A mixture of 2,4-dinitrophenol (85 wt %, 6.72 g, 31 mmol), octadecyl bromide (20.7 g, 62 mmol), sodium carbonate (6.57 g, 62 mmol) and dimethylformamide (31 mL) was heated to 100° C. under a nitrogen atmosphere for 22 h. The cooled mixture was diluted with water (200 mL), acidified with 10N hydrochloric acid (50 mL) and extracted with ether. The extracts were washed with water and brine, and dried over magnesium sulfate. The solvent was removed and the solid recrystallized to give 1-octadecyloxy-2,4-dinitrobenzene (10.7 g, 79%): mp 63.5°-64.0° C.

Source