Hydroxylamine → alpha-Phenylbenzoin oxime

HRID 2295965

Reaktionsgleichung

Reaktionsgleichung von HRID 2295965
C1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[OH:16])=O)C=CC=CC=1.[NH2:23][OH:24].Cl.NO.[C:28]([O-])(=O)[CH3:29].[Na+]>O.CO>[C:29]1([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([OH:16])[C:13](=[N:23][OH:24])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=2)[CH:28]=[CH:9][CH:8]=[CH:7][CH:12]=1

Komponenten

7

Edukt 4

HCID 787Hydroxylamine2×HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19793701Phenylbenzoin3×

Produkt 1

HCID 73998057alpha-Phenylbenzoin oximeAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

180 g (0.625 mol) 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 result solution was added to the phenylbenzoin and the reaction mixtur 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 extracted 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 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:

Aufarbeitung

  1. customround bottomed flask fitted with a reflux condenser
  2. customwas prepared
  3. additionby treating 177.9 g
  4. additionwas added
  5. temperatureThe solution was cooled
  6. filtrationfiltered
  7. extractionextracted
  8. additiontreated with refluxing hexane
  9. waitAfter 72 hours the solid remaining in the extraction thimble
  10. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-0c075adba5a34f31b0eadffc69001a52
Quelldatensatz
uspto-grants-1984_01
Patentnummer
US04427594

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