Reaction #452472

Reaction equation

water

1,2-Dibromoethane

potassium carbonate

3-nitrocatechol

→

product

Yield 32.7%

5-Nitro-2,3-dihydro-1,4-benzodioxin

Yield 32.7%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe solution was heated
2. 2
   Washwashed with 2N
3. 3
   Dryingsodium hydroxide solution (150 ml), dried (Na2SO4)
4. 4
   Otherevaporated in vacuo
5. 5
   Otherto give an orange oil
6. 6
   OtherPurification by column chromatography (silica; ether)

Procedure

1,2-Dibromoethane (12.0 g, 0.064 mol), potassium carbonate (17.6 g, 0.127 mol) and tetra-n-butyl ammonium bromide (1.37 g, 0.0043 mol) were added to a stirred solution of 3-nitrocatechol (6.59 g, 0.043 mol) in toluene (210 ml). The solution was heated at reflux with azeotropic removal of water for 23 h, cooled to room temperature, washed with 2N. sodium hydroxide solution (150 ml), dried (Na2SO4), and evaporated in vacuo to give an orange oil. Purification by column chromatography (silica; ether) gave the product (2.55 g), m.p. 55-59° C.

Source