Cyclohexane → HCID 85893940, compound

HRID 1703551Notes

Reaction equation

HRID 1703551 reaction equation
Br[C:2]1([CH2:17][C:18]([OH:20])=[O:19])[O:10][C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1CCCCC1.[N+:27]([O-:32])([N+]([O-])=O)=[O:28]>C(Cl)(Cl)Cl>[N+:27]([C:2]1([CH2:17][C:18]([OH:20])=[O:19])[O:10][C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-:32])=[O:28]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 25352Nitrogen oxide (N2O4)HCID 70609418HCID 70609418, compound

Product 1

HCID 85893940HCID 85893940, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 2-bromo-3-phenyl-4-benzofuranacetic acid (12.1 g., 0.0365 mole) and cyclohexane (3.3 g., 0.04 mole) in 100 ml. of chloroform is treated with 5 g. of dinitrogen tetroxide in 20 ml. of chloroform dropwise. The mixture is stirred for 16 hours at about 25° C. then at 50°-55° C. for about 20 minutes. The mixture is washed with water, and the organic layer is treated with an aqueous base. The aqueous layer is acidified, then extracted with dichloromethane. The organic layer is washed thrice with water, dried and evaporated. Two recrystallizations from benzene give light yellow solid 2-nitro-3-phenyl-4-benzofuranacetic acid, m.p. 187.5°-189.5° C.

Workup

  1. waitat 50°-55° C. for about 20 minutes
  2. washThe mixture is washed with water
  3. additionthe organic layer is treated with an aqueous base
  4. extractionextracted with dichloromethane
  5. washThe organic layer is washed thrice with water
  6. customdried
  7. customevaporated
  8. customTwo recrystallizations from benzene

Sources & evidence

ORD record
ord-e7e9fab63a1942be89035f473b0d32f3
Source dataset
uspto-grants-1978_11
Patent number
US04124704

Reaction notes

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