Hydrogen Peroxide → HCID 22475868, compound

HRID 1734710Notes

Reaction equation

HRID 1734710 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].[CH3:25][CH:26]([CH3:29])[CH2:27][PH2:28].[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:28](=[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])[CH2:27][CH:26]([CH3:29])[CH3:25])=[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; 1.6M) of butyllithium are added dropwise over 30 minutes under nitrogen at 0° C. 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 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 (2-methylprop-1-yl)phosphine in 200 ml of tetrahydrofuran. After stirring for 2 h at -30° C., the yellow solution is warmed to room temperature and washed once with water. The organic phase is dried over magnesium sulfate, filtered, and the filtrate is concentrated 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 to the solution. The mixture is stirred for 2 h and washed first with water and then with a saturated solution of sodium hydrogencarbonate and afterwards dried over magnesium sulfate and filtered. The solution is concentrated on a rotary evaporator. Crystallisation of the residue from hexane gives 27.8 g (68.5% of theory) of the above compound as a yellow powder with a melting point of 85°-86 ° C.

Workup

  1. temperaturethe yellow solution is warmed to room temperature
  2. washwashed once with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated on a rotary evaporator
  6. dissolutionThe residue is dissolved in 200 ml of toluene
  7. stirringThe mixture is stirred for 2 h
  8. washwashed first with water
  9. dry with materialwith a saturated solution of sodium hydrogencarbonate and afterwards dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe solution is concentrated on a rotary evaporator
  12. customCrystallisation of the residue from hexane

Sources & evidence

ORD record
ord-9c06bfc2fc484b21a7122a5bac2e7585
Source dataset
uspto-grants-1996_07
Patent number
US05534559

Reaction notes

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