Methane → HCID 54070985, compound

HRID 1391355Notes

Reaction equation

HRID 1391355 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:45])([F:44])[C:17]([F:43])([F:42])[C:18]([F:41])([F:40])/[CH:19]=[CH:20]/[C:21]([F:39])([F:38])[C:22]([F:37])([F:36])[C:23]([F:35])([F:34])[C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([N+:31]([O-])=O)[CH:25]=2)=[CH:12][C:11]=1[N+:46]([O-])=O.C>O.CO.C1(C)C=CC=CC=1.C(=O)=O>[OH:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:35])[C:22]([F:36])([F:37])[C:21]([F:38])([F:39])[CH:20]=[CH:19][C:18]([F:40])([F:41])[C:17]([F:42])([F:43])[C:16]([F:44])([F:45])[C:13]2[CH:14]=[CH:15][C:10]([OH:9])=[C:11]([NH2:46])[CH:12]=2)=[CH:25][C:26]=1[NH2:31]

Participants

8

Reactant 3

HCID 297MethaneHCID 24489Sodium Dithionite2×HCID 21331009HCID 21331009, compound

Product 1

HCID 54070985HCID 54070985, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 280Carbon DioxideSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 1140TolueneSolvent

Procedure

Sodium dithionite (10 g) in 30 ml of water was added slowly with stirring at room temperature to a solution of 1.0 g (0.0017 mole) of trans-1,2-bis[3-(4-hydroxy-3-nitrophenyl)perfluoropropyl]ethylene (prepared as described in Example I) in 250 ml of methanol. The methanolic solution turned bright yellow and then slowly faded to water-white as reduction occurred. After addition of the sodium dithionite was completed, stirring was continued for an additional 30 minutes at which time water was added, resulting in a total solution volume of 750 ml. The resultant white slurry was extracted three times with 200 ml portions of ether and the combined ether extracts were washed repeatedly with water. The ether solution was then dried over anhydrous magnesium sulfate and stripped to dryness under reduced pressure to give a white residue. Most of this solid was soluble in 900 ml of hot toluene which was treated with charcoal and reduced in volume to 100 ml. Cooling in dry ice gave 0.5 g (55% yield) of the olefinic product as white platelets, mp 187°-188° C.

Workup

  1. additionwas added
  2. customresulting in a total solution volume of 750 ml
  3. extractionThe resultant white slurry was extracted three times with 200 ml portions of ether
  4. washthe combined ether extracts were washed repeatedly with water
  5. dry with materialThe ether solution was then dried over anhydrous magnesium sulfate
  6. customto give a white residue

Sources & evidence

ORD record
ord-b1a1b5eb73fe49d09e9362c96506d4d7
Source dataset
uspto-grants-1979_02
Patent number
US04142037

Reaction notes

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