Reaktion #56367

Reaktionsgleichung

phenylbenzoin

phenylbenzoin

hydroxylamine

sodium acetate

hydroxylamine hydrochloride

hydroxylamine

phenylbenzoin

→

alpha-phenylbenzoin oxime

Ausbeute 40.0%

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeround bottomed flask fitted with a reflux condenser
2. 2
   Sonstigewas prepared
3. 3
   workup.ADDITIONby treating 177.9 g
4. 4
   workup.ADDITIONwas added
5. 5
   TemperaturThe solution was cooled
6. 6
   Filtrationfiltered
7. 7
   workup.ADDITIONtreated with refluxing hexane
8. 8
   workup.WAITAfter 72 hours the solid remaining in the extraction thimble
9. 9
   Sonstigewas collected

Vorschrift

180 g (0.625 mole) of phenylbenzoin was added to a 3 liter, one necked, round bottomed flask fitted with a reflux condenser and a nitrogen bypass. 1.45 liters of methanol was added to dissolve the phenylbenzoin and free hydroxylamine was prepared by treating 177.9 g. (2.56 moles) hydroxylamine hydrochloride with 209.9 g (2.56 moles) of sodium acetate in water. The resultant solution was added to the phenylbenzoin and the reaction mixture was stirred for 48 hours at reflux at which time an additional 1.24 moles of hydroxylamine was added. The solution was cooled and filtered. The solids were then placed in a Soxhlet extractor and treated with refluxing hexane. After 72 hours the solid remaining in the extraction thimble was collected to yield 40% of the theoretical yield of pure alpha-phenylbenzoin oxime, m.p. 150°-52° C. (lit. 153.5) The hexane extract can be concentrated to yield unreacted phenylbenzoin (50% of theory) which may be recycled to afford additional phenylbenzoin oxime. This material was employed to polymerize 2,6-xylenol using the following composition:

Quelle