Hydrogen Peroxide → HCID 20300906, compound

HRID 1733269Notes

Reaction equation

HRID 1733269 reaction equation
C(OC(=O)C)(=[O:3])C.OO.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([CH3:31])[CH2:22][N:23]2[CH2:28][CH:27]([CH3:29])[O:26][CH:25]([CH3:30])[CH2:24]2)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11]>[OH-].[K+]>[C:10]([C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH:21]([CH3:31])[CH2:22][N+:23]2([O-:3])[CH2:24][CH:25]([CH3:30])[O:26][CH:27]([CH3:29])[CH2:28]2)=[CH:18][CH:19]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 916954-(3-(4-(1,1-Dimethylethyl)phenyl)-2-methylpropyl)-2,6-dimethylmorpholine

Product 1

HCID 20300906HCID 20300906, compound

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 120 ml of acetic anhydride and 120 ml of 30% hydrogen peroxide is added dropwise to 40 g of 4-[3-(p-tert.-butyl-phenyl)-2-methyl-propyl]-2,6-dimethyl-morpholine while cooling with an ice-bath so that the temperature does not exceed 45°-50° C. After stirring at room temperature for 16 hours, the mixture is cooled to -10° C. and treated with 280 ml of 40% potassium hydroxide solution, exhaustively extracted with chloroform and concentrated in vacuo at 30° C. (bath temperature). The residue is stirred at room temperature with 2-N sodium hydroxide solution for 16 hours and again extracted several times with chloroform. The combined chloroform extracts are washed neutral with sodium chloride solution, dried over sodium sulphate and evaporated. The highly viscous, syrupy residue is crystallised from ether/pentane. There is obtained pure 4-[3-(p-tert.butyl-phenyl)-2-methyl-propyl]-2,6-dimethyl-morpholine-4-oxide in the form of the hydrate; melting point 115°-118° C.

Workup

  1. temperaturewhile cooling with an ice-bath so that the temperature
  2. customdoes not exceed 45°-50° C
  3. temperaturethe mixture is cooled to -10° C.
  4. extractionexhaustively extracted with chloroform
  5. concentrationconcentrated in vacuo at 30° C. (bath temperature)
  6. stirringThe residue is stirred at room temperature with 2-N sodium hydroxide solution for 16 hours
  7. washThe combined chloroform extracts are washed neutral with sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. customevaporated
  10. customThe highly viscous, syrupy residue is crystallised from ether/pentane

Sources & evidence

ORD record
ord-16795af39fd346aa96334bfa54198ded
Source dataset
uspto-grants-1980_12
Patent number
US04241058

Reaction notes

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