Hydrogen Peroxide → HCID 22475868, compound

HRID 2259323Notes

Reaction equation

HRID 2259323 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(N[CH:10]([CH3:12])[CH3:11])(C)C.[CH3:13][C:14]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:15]=1[C:16](Cl)=[O:17].[CH2:25]([PH2:29])[CH:26]([CH3:28])[CH3:27].[OH:30]O.[O:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH3:33][C:34]1[CH:1]=[C:2]([CH3:3])[CH:12]=[C:10]([CH3:11])[C:35]=1[C:36]([P:29](=[O:30])([C:16](=[O:17])[C:15]1[C:14]([CH3:13])=[CH:22][C:21]([CH3:23])=[CH:20][C:19]=1[CH3:24])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:32]

Participants

7

Reactant 6

HCID 784Hydrogen PeroxideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451630Phosphine, (2-methylpropyl)-HCID 178418339Butyllithium

Product 1

HCID 22475868HCID 22475868, compound

Conditions

Temperature
-30 °C

Procedure

140.6 ml (0.225 mol, 1.6 M) of butyllithium are added dropwise under nitrogen at 0° C. over the course of 30 minutes to a solution of 31.9 ml (0.225 mol) of diisopropylamine in 80 ml of tetrahydrofuran. This solution is added dropwise at -30° C. over the course of 90 minutes to a solution of 41.1 g (0.225 mol) of 2,4,6-trimethylbenzoyl chloride and 12 ml (0.102 mol) of isobutylphosphine in 200 ml of tetrahydrofuran. After the mixture has been stirred for 2 hours at -30° C., the yellow solution is allowed to warm to room temperature and is washed once with water. The organic phase is dried using magnesium sulfate, filtered and evaporated on a rotary evaporator. The residue is dissolved in 200 ml of toluene, and 11.6 g (0.102 mol) of 30% hydrogen peroxide are added. After the mixture has been stirred for 2 hours, it is washed first with water then with saturated sodium hydrogen carbonate solution. The organic phase is then dried using magnesium sulfate and filtered, and the solution is evaporated on a rotary evaporator. Crystallisation from hexane gives 27.8 g (68.5% of theory) of the abovementioned compound as a yellow powder. The melting point is 85°-86° C.

Workup

  1. temperatureto warm to room temperature
  2. washis washed once with water
  3. customThe organic phase is dried
  4. filtrationfiltered
  5. customevaporated on a rotary evaporator
  6. dissolutionThe residue is dissolved in 200 ml of toluene
  7. stirringAfter the mixture has been stirred for 2 hours
  8. washit is washed first with water
  9. customThe organic phase is then dried
  10. filtrationfiltered
  11. customthe solution is evaporated on a rotary evaporator
  12. customCrystallisation from hexane

Sources & evidence

ORD record
ord-e919672af90f4e9c96c2bb9883ab9a46
Source dataset
uspto-grants-1995_12
Patent number
US05472992

Reaction notes

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