Cyclohexane → HCID 20333854, compound

HRID 1833690Notes

Reaction equation

HRID 1833690 reaction equation
Br[C:2]1[O:3][C:4]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:5]=2[C:6]=1[C:7]1[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=1.C1CCCCC1.[N+:28]([O-:33])([N+]([O-])=O)=[O:29]>C(Cl)(Cl)Cl>[Cl:21][C:18]1[CH:19]=[CH:20][C:4]2[O:3][C:2]([N+:28]([O-:33])=[O:29])=[C:6]([C:7]3[CH:8]=[C:9]([CH2:13][C:14]([OH:16])=[O:15])[CH:10]=[CH:11][CH:12]=3)[C:5]=2[CH:17]=1

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 25352Nitrogen oxide (N2O4)HCID 20333853HCID 20333853, compound

Product 1

HCID 20333854HCID 20333854, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3-(2-bromo-5-chloro-3-benzofuranyl)phenylacetic acid in chloroform with 1.5 equivalents of cyclohexane is treated with 1.5 equivalents of dinitrogen tetroxide and stirred for about 20 hours at room temperature. The mixture is washed with water, extracted with saturated sodium bicarbonate solution, then the aqueous extracts are acidified. The mixture is extracted with dichloromethane, which is dried and concentrated. The residue is recrystallized from a mixture of benzene and hexane to provide 3-(5-chloro-2-nitro-3-benzofuranyl)phenylacetic acid.

Workup

  1. washThe mixture is washed with water
  2. extractionextracted with saturated sodium bicarbonate solution
  3. extractionThe mixture is extracted with dichloromethane, which
  4. customis dried
  5. concentrationconcentrated
  6. customThe residue is recrystallized from a mixture of benzene and hexane

Sources & evidence

ORD record
ord-18f33c65853545ecaffca25f752e6073
Source dataset
uspto-grants-1978_01
Patent number
US04066782

Reaction notes

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