Hydrogen Peroxide → HCID 22117941, compound

HRID 1275855Notes

Reaction equation

HRID 1275855 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:13]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[C:28]([O:36][CH3:37])[CH:27]=2)[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].OO.S([O-])([O-])=[O:41].[Na+].[Na+]>C(Cl)Cl.C(O)C>[CH3:21][O:20][C:18]1[CH:19]=[C:14]([P:13](=[O:41])([C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:26]2[CH:27]=[C:28]([O:36][CH3:37])[C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=2)[CH:15]=[C:16]([O:24][CH3:25])[C:17]=1[O:22][CH3:23]

Participants

6

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 24437Sodium SulfiteHCID 22117932HCID 22117932, compound

Product 1

HCID 22117941HCID 22117941, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

31.6 g (59.3 mmol) of tris(3,4,5-trimethoxyphenyl)phosphine were dissolved in a mixture of 100 ml of methylene chloride and 150 ml of ethanol in a 500 ml four-necked sulphonation flask having a thermometer, mechanical stirrer, 100 ml dropping funnel and condenser. 6.8 g (60 mmol) of 30% hydrogen peroxide were added dropwise to the resulting solution within 15 min., with the reaction temperature being held at 15-20° C. Shortly after completion of the dropwise addition of hydrogen peroxide the reaction had finished according to TLC. The reaction solution obtained was treated with 5 ml of saturated sodium sulphite solution, following which peroxide could no longer be detected in the reaction mixture. The reaction mixture was treated with 200 ml of methylene chloride and extracted twice with 300 ml of deionized water. The combined phases were re-extracted with 300 ml of methylene chloride, washed with 300 ml of saturated sodium chloride solution, dried over magnesium sulphate, filtered and treated with 200 ml of hexane. The solution obtained was concentrated on a RV at 50° C./600 mbar, with crystallization setting in. After stirring at 0° C. for 2 h. the crystalline material was filtered off under suction, washed twice with 50 ml of hexane and dried for 2 h. at 100° C. in a HV. 13.0 g of tris(3,4,5-trimethoxyphenyl)phosphine oxide were isolated at a first crystallizate. A further 12.7 g of tris(3,4,5-trimethoxyphenyl)phosphine oxide were obtained from the mother liquor as a second crystallizate. Both crystallizates were identical and uniform. The total yield of tris(3,4,5-trimethoxyphenyl)phosphine oxide was 25.7 g (79%).

Workup

  1. custombeing held at 15-20° C
  2. customThe reaction solution obtained
  3. extractionextracted twice with 300 ml of deionized water
  4. extractionThe combined phases were re-extracted with 300 ml of methylene chloride
  5. washwashed with 300 ml of saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. additiontreated with 200 ml of hexane
  9. customThe solution obtained
  10. concentrationwas concentrated on a RV at 50° C./600 mbar
  11. customwith crystallization setting in
  12. filtrationwas filtered off under suction
  13. washwashed twice with 50 ml of hexane
  14. customdried for 2 h. at 100° C. in a HV

Sources & evidence

ORD record
ord-5e40d884fdff40998a74036c688659f1
Source dataset
uspto-grants-2000_12
Patent number
US06162929

Reaction notes

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