Water → HCID 21330915, compound

HRID 1391323Notes

Reaction equation

HRID 1391323 reaction equation
Br[C:2]1[O:3][C:4]2[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([CH3:14])[CH:8]=1.C1CCC(C(O)=O)CC=1.[N+:28]([O-:33])([N+]([O-])=O)=[O:29].O>C(O)(=O)C.C(Cl)(Cl)(Cl)Cl>[CH3:14][C:9]1[CH:8]=[C:7]([C:6]2[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[O:3][C:2]=2[N+:28]([O-:33])=[O:29])[CH:12]=[CH:11][C:10]=1[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 21330927HCID 21330927, compound

Product 1

HCID 21330915HCID 21330915, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 12.4 g (0.041 mole) of 2-bromo-3-(3',4'-dimethylphenyl)benzofuran in 400 ml of acetic acid is added 7.8 g (0.062 mole) of cyclohexene-4-carboxylic acid and a solution of 5 g (0.062 mole) of dinitrogen tetroxide in 25 ml of acetic acid. After stirring for about 16 hours the mixture is poured into cold water to give a gummy solid. The solid is collected, washed with water and dissolved in diethyl ether. The ether solution is washed with water, 10% sodium bicarbonate solution and saturated sodium chloride solution, then dried. Evaporation provides a residue which is dissolved in carbon tetrachloride and chromatographed on silica gel, eluting with carbon tetrachloride and combining the fractions consisting of chiefly one component according to thin layer chromatography. The solid is recrystallized from aqueous ethanol, then from isopropanol to provide yellow solid 3-(3',4'-dimethylphenyl)-2-nitrobenzofuran, m.p. 125°-133° C. which is about 90% pure, containing about 10% of monobromo-3-(3',4'-dimethylphenyl)-2-nitrobenzofuran.

Workup

  1. customto give a gummy solid
  2. customThe solid is collected
  3. washwashed with water
  4. dissolutiondissolved in diethyl ether
  5. washThe ether solution is washed with water, 10% sodium bicarbonate solution and saturated sodium chloride solution
  6. customdried
  7. customEvaporation
  8. customprovides a residue which
  9. customchromatographed on silica gel
  10. washeluting with carbon tetrachloride
  11. customThe solid is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-4c3d418433154a96bc22a8c64fc73330
Source dataset
uspto-grants-1979_02
Patent number
US04141990

Reaction notes

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