Acetic Acid → 5,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

HRID 46625

Reaction equation

HRID 46625 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[C:15]3[O:17][CH2:18][O:19][C:14]3=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)C.C1CCC(C(O)=O)CC=1.[N+:33]([O-:38])([N+]([O-])=O)=[O:34]>O>[CH2:18]1[O:17][C:15]2=[CH:16][C:4]3[O:3][C:2]([N+:33]([O-:38])=[O:34])=[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=3[CH:13]=[C:14]2[O:19]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 544242002-Bromo-5,6-methylenedioxy-3-phenylbenzofuran

Product 1

HCID 541688035,6-Methylenedioxy-2-nitro-3-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 5.2 g. (0.016 mole) of 2-bromo-5,6-methylenedioxy-3-phenylbenzofuran in 225 ml. of acetic acid is added with stirring 5.0 g. (0.024 mole) of cyclohexene-4-carboxylic acid, then 2.2 g. (0.024 mole) of dinitrogen tetraoxide in 25 ml. of acetic acid. After about one hour the mixture is poured into cold water, and the yellow product is collected and washed with water. The product is dissolved in dichloromethane, and the solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution, then dried. The solution is concentrated to dryness to provide a yellow residue which is recrystallized from a benzene-hexane mixture, then from an isopropanol-benzene mixture to provide yellow needles of 5,6-methylenedioxy-2-nitro-3-phenylbenzofuran, m.p. 180°-183° C.

Workup

  1. customthe yellow product is collected
  2. washwashed with water
  3. dissolutionThe product is dissolved in dichloromethane
  4. washthe solution is washed with cold 5 percent sodium hydroxide solution, water and saturated sodium chloride solution
  5. customdried
  6. concentrationThe solution is concentrated to dryness
  7. customto provide a yellow residue which
  8. customis recrystallized from a benzene-hexane mixture

Sources & evidence

ORD record
ord-a38d89104c9f443cab73e1460278556b
Source dataset
uspto-grants-1979_11
Patent number
US04174403

Linked notes

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