Methane → HCID 54070985, compound

Participants

Reaction Steps

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.

Provenance & Evidence