Water → HCID 21320324, compound

HRID 1834045Notes

Reaction equation

HRID 1834045 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCCCC=1.[N+:26]([O-:31])([N+]([O-])=O)=[O:27].O>C(O)(=O)C>[N+:26]([C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][C:5]=2[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([O-:31])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8079CyclohexeneHCID 25352Nitrogen oxide (N2O4)HCID 22761703HCID 22761703, compound

Product 1

HCID 21320324HCID 21320324, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of 20 g (0.063 mole) of 2-bromo-3-phenyl-5-benzofurancarboxylic acid and 1.25 l of acetic acid is stirred and heated to 55° C. To this mixture is added 7.7 g (0.094 mole) of cyclohexene. To this mixture is added dropwise 8.7 g (0.094 mole) of dinitrogen tetroxide in 25 ml of acetic acid. After 5 hours the mixture is poured into cold water and the solid product is collected. Recrystallization from aqueous ethanol followed by recrystallization from a benzene-ethanol mixture provides 2-nitro-3-phenyl-5-benzofurancarboxylic acid, m.p. 271°-273° C.

Workup

  1. customthe solid product is collected
  2. customRecrystallization from aqueous ethanol
  3. customfollowed by recrystallization from a benzene-ethanol mixture

Sources & evidence

ORD record
ord-f59f405228fb4f9a9ddfe10cb8331615
Source dataset
uspto-grants-1978_01
Patent number
US04067993

Reaction notes

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