Water → HCID 21330916, compound

HRID 1391321Notes

Reaction equation

HRID 1391321 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCC(C(O)=O)CC=1.[N+:27]([O-:32])([N+]([O-])=O)=[O:28].O>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:2]([N+:27]([O-:32])=[O:28])[O:3][C:4]=2[CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 21319883HCID 21319883, compound

Product 1

HCID 21330916HCID 21330916, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4 g (0.014 mole) of 2-bromo-6-methyl-3-phenylbenzofuran in 50 ml of acetic acid and 50 ml of chloroform is added 1.8 g (0.015 mole) of cyclohexene-4-carboxylic acid and a solution of 1.4 g (0.015 mole) of dinitrogen tetroxide in 10 ml of acetic acid. After sitting for about 16 hours the mixture is poured into water. This mixture is extracted with chloroform and the extracts are washed with water and 10% sodium bicarbonate solution and dried. Evaporation of the solvent and recrystallization of the residue from cyclohexane provides yellow crystals of 6-methyl-2-nitro-3-phenylbenzofuran, m.p. 142°-144° C.

Workup

  1. extractionThis mixture is extracted with chloroform
  2. washthe extracts are washed with water and 10% sodium bicarbonate solution
  3. customdried
  4. customEvaporation of the solvent and recrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-3c9189e8bb3e481c9508d23d20603b0e
Source dataset
uspto-grants-1979_02
Patent number
US04141990

Reaction notes

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