Toluene → HCID 13772931, compound

HRID 980568Notes

Reaction equation

HRID 980568 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=[C:6]([Cl:9])[C:7]=1Cl.[C:13]1([C:19]2[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=2[CH2:21][OH:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].O.CCCCCC>[Cl:9][C:6]1[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=[C:2]([Cl:1])[C:7]=1[O:22][CH2:21][C:20]1[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 76229(1,1'-Biphenyl)-2-methanolHCID 883653,4,5-Trichloronitrobenzene

Product 1

HCID 13772931HCID 13772931, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

Into a 250 milliliter reaction flask equipped with a magnetic stirrer was added 10.04 grams (0.044 moles) of 3,4,5-trichloronitrobenzene, 8.16 grams (0.044 moles) of 2-phenylbenzyl alcohol, 1.29 grams (0.004 moles) of tetra-N-butylammonium bromide, 80 milliliters of toluene and aqueous sodium hydroxide (5.28 grams in 6.6 milliliters of water). The resulting mixture was stirred vigorously at ambient temperature overnight. The mixture was then diluted with water and filtered. The layers were separated and the organic layer was washed twice with water and finally once with a saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the mixture was concentrated under vacuum to give a red-orange oil which was stirred into hexane. Crystallization from the hexane and filtration afforded a yellow-orange powder having a melting point of 83.0° C.-84.5° C.

Workup

  1. customInto a 250 milliliter reaction flask
  2. customequipped with a magnetic stirrer
  3. filtrationfiltered
  4. customThe layers were separated
  5. washthe organic layer was washed twice with water and finally once with a saturated aqueous sodium chloride solution
  6. dry with materialAfter drying over anhydrous sodium sulfate
  7. concentrationthe mixture was concentrated under vacuum
  8. customto give a red-orange oil which
  9. customCrystallization
  10. filtrationfrom the hexane and filtration
  11. customafforded a yellow-orange powder

Sources & evidence

ORD record
ord-20d004fa32754bb38bd7de154d5e8da2
Source dataset
uspto-grants-1987_01
Patent number
US04638088

Reaction notes

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