Hydroxylamine → alpha-Phenylbenzoin oxime

HRID 838833

Reaction equation

HRID 838833 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 73998057alpha-Phenylbenzoin oximeYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

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 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:

Workup

  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. additiontreated with refluxing hexane
  8. waitAfter 72 hours the solid remaining in the extraction thimble
  9. customwas collected

Sources & evidence

ORD record
ord-1a5619b5de404e9684e45e1ea6da538c
Source dataset
uspto-grants-1978_06
Patent number
US04093598

Linked notes

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