Methane → HCID 11069315, compound

HRID 1637050Notes

Reaction equation

HRID 1637050 reaction equation
[N+:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=4)=[CH:17][C:16]=3[CH3:31])=[C:11]([CH3:32])[CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.O.C>CN(C=O)C.[Pt]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][C:7]4[CH:33]=[CH:34][C:4]([NH2:1])=[CH:5][CH:6]=4)=[CH:10][C:11]=3[CH3:32])=[C:16]([CH3:31])[CH:17]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 962WaterHCID 15456986HCID 15456986, compound

Product 1

HCID 11069315HCID 11069315, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

4,4'-Bis(4-nitrophenoxy)-2,2'-dimethylbiphenyl (80 g) was dissolved in 350 ml of DMF and added carefully to a hydrogenation bottle containing 8 gm of 5% Pt/C. The solution was subjected to hydrogenation at 100° C. for 3 hours. Then 100 ml of water and 3 g of decolorizing charcoal were added and heated for 5 min. The solution was then filtered through a Celite pad and 1000 ml of water was added. The reaction mixture became a mixture of fluffy solid and a sticky resin and was stirred for 1 hour to give a tan colored solid. The solid was removed by filtration, crushed with a mortar and pestel and then stirred with 1000 ml of water for 1 hour. The solid was collected by filtration and dried to afford 59.2 g (85%) of the product mp=140° C.

Workup

  1. additionadded carefully to a hydrogenation bottle
  2. temperatureheated for 5 min
  3. filtrationThe solution was then filtered through a Celite pad and 1000 ml of water
  4. additionwas added
  5. additiona mixture of fluffy solid
  6. customto give a tan colored solid
  7. customThe solid was removed by filtration
  8. customcrushed with a mortar and pestel
  9. stirringstirred with 1000 ml of water for 1 hour
  10. filtrationThe solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-0099f871ec7b433ca26b101983770c8e
Source dataset
uspto-grants-2000_03
Patent number
US06037499

Reaction notes

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