3-Cyclohexene-1-carboxylic acid → HCID 21320309, compound

HRID 262221Notes

Reaction equation

HRID 262221 reaction equation
Br[C:2]1[O:3][C:4]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:19])=[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+:29]([O-:34])([N+]([O-])=O)=[O:30]>C(Cl)(Cl)Cl>[OH:19][CH2:18][CH2:17][C:14]1[CH:15]=[CH:16][C:4]2[O:3][C:2]([N+:29]([O-:34])=[O:30])=[C:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:5]=2[CH:13]=1

Participants

5

Reactant 3

HCID 209033-Cyclohexene-1-carboxylic acidHCID 25352Nitrogen oxide (N2O4)2×HCID 21320312HCID 21320312, compound

Product 1

HCID 21320309HCID 21320309, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

The product from step B is mixed with 8.83 g. (0.07 mole) of cyclohexene-4-carboxylic acid in 175 ml. of chloroform, and 6.5 g. (0.07 mole) of dinitrogen tetraoxide in 15 ml. of chloroform is added dropwise. After 30 minutes an additional 1.0 g. of dinitrogen tetraoxide in 5 ml. of chloroform is added, and the mixture is stirred for about 18 hours. The mixture is washed twice with water, twice with saturated sodium bicarbonate solution and twice again with water, then dried. Evaporation to dryness provides a residue which is recrystallized from aqueous ethanol, then benzene, to provide 5-(2-hydroxyethyl)-2-nitro-3-phenylbenzofuran as a yellow solid, m.p. 169°-173° C.

Workup

  1. washThe mixture is washed twice with water, twice with saturated sodium bicarbonate solution and twice again with water
  2. customdried
  3. customEvaporation to dryness
  4. customprovides a residue which
  5. customis recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-6c91c419c0d9498882b5121cb490459d
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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