Hydrogen Peroxide → HCID 18513614, compound

HRID 1369361Notes

Reaction equation

HRID 1369361 reaction equation
C([Li])CCC.[CH2:6]([PH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:7]([CH3:9])[CH3:8].[CH3:17][C:18]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:19]=1[C:20](Cl)=[O:21].[OH:29]O>O1CCCC1>[CH3:17][C:18]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:19]=1[C:20]([P:10](=[O:29])([CH2:6][CH:7]([CH3:9])[CH3:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:21]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 16703377(2-Methylpropyl)(phenyl)phosphaneHCID 178418339Butyllithium

Product 1

HCID 18513614HCID 18513614, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At −20° C., 40 ml (0.064 mol) of butyllithium 1.6 M are slowly added dropwise to 9.5 g (0.058 mol) of isobutylphenylphosphine in 100 ml of tetrahydrofuran (THF). At the same temperature, 11.7 g (0.064 mol) of 2,4,6-trimethylbenzoyl chloride are then added dropwise. After the mixture has been allowed to warm to room temperature, the orange reaction suspension is concentrated using a rotary evaporator (Rotavap). The residue is taken up in 150 ml of toluene, and is treated with 13.1 g (0.116 mol) of hydrogen peroxide 30%. After the mixture has been stirred for 2 hours between 20-30° C., the reaction is complete. The reaction emulsion is poured onto water and washed with aqueous saturated sodium hydrogencarbonate solution, then dried over magnesium sulfate and filtered. The filtrate is concentrated using the Rotavap. The residue is purified over silica gel and dried under a high vacuum. 11.8 g of the title compound are obtained as a yellow viscous oil.

Workup

  1. concentrationthe orange reaction suspension is concentrated
  2. customa rotary evaporator (Rotavap)
  3. additionThe reaction emulsion is poured onto water
  4. washwashed with aqueous saturated sodium hydrogencarbonate solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate is concentrated
  8. customThe residue is purified over silica gel
  9. customdried under a high vacuum

Sources & evidence

ORD record
ord-3925718f6e6140ff865fb86af745563d
Source dataset
uspto-grants-2003_06
Patent number
US06579663B2

Reaction notes

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