Water → HCID 21330914, compound

HRID 1391324Notes

Reaction equation

HRID 1391324 reaction equation
I[C:2]1[O:3][C:4]2[C:16]([CH3:17])=[CH:15][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>[CH3:17][C:16]1[C:4]2[O:3][C:2]([N+:27]([O-:32])=[O:28])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)HCID 21330920HCID 21330920, compound

Product 1

HCID 21330914HCID 21330914, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution of 5.0 g (0.015 mole) of 2-iodo-7-methyl-3-phenylbenzofuran from Example 9 in 100 ml of acetic acid is added 2.8 g (0.022 mole) of cyclohexene-4-carboxylic acid, then dropwise 2.0 g (0.022 mole) of dinitrogen tetroxide in 10 ml of acetic acid. The mixture is poured into cold water, then extracted with diethyl ether. The ether extracts are washed with water, 5% sodium hydroxide solution, water and saturated sodium chloride solution and dried. The extracts are then concentrated to provide a solid residue which is recrystallized from aqueous ethanol to provide yellow crystals of 7-methyl-2-nitro-3-phenylbenzofuran, m.p. 122°-127° C., which is shown to be identical to the product of Example 2 by its infrared spectrum.

Workup

  1. extractionextracted with diethyl ether
  2. washThe ether extracts are washed with water, 5% sodium hydroxide solution, water and saturated sodium chloride solution
  3. customdried
  4. concentrationThe extracts are then concentrated
  5. customto provide a solid residue which
  6. customis recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-bd94876061b94442acf6f8fdf61e37be
Source dataset
uspto-grants-1979_02
Patent number
US04141990

Reaction notes

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