Water → 5-Nitro-2,3-dihydro-1,4-benzodioxine

HRID 726540Notes

Reaction equation

HRID 726540 reaction equation
Br[CH2:2][CH2:3]Br.C(=O)([O-])[O-].[K+].[K+].[N+:11]([C:14]1[CH:20]=[CH:19][CH:18]=[C:16]([OH:17])[C:15]=1[OH:21])([O-:13])=[O:12].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[N+:11]([C:14]1[C:15]2[O:21][CH2:3][CH2:2][O:17][C:16]=2[CH:18]=[CH:19][CH:20]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 4675622Nitrocatechol

Product 1

HCID 122313185-Nitro-2,3-dihydro-1,4-benzodioxineYield 32.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

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.

Workup

  1. temperatureThe solution was heated
  2. washwashed with 2N sodium hydroxide solution (150 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give an orange oil
  6. customPurification by column chromatography (silica; ether)

Sources & evidence

ORD record
ord-973b92ffb35144e492a39e26b7b6f2a7
Source dataset
uspto-grants-1998_01
Patent number
US05710149

Reaction notes

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