Hydrochloric Acid → HCID 14906785, compound

HRID 376081Notes

Reaction equation

HRID 376081 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].OO.[O-:26]S([O-])=O.[Na+].[Na+].Cl>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([P:11](=[O:26])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 13087640HCID 13087640, compound

Product 1

HCID 14906785HCID 14906785, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

da) 75 g of 3,4-dimethoxyphenyl-diphenylphosphine were taken up in 300 ml of methanol. 29.3 ml of 35% H2O2 solution were added dropwise to the suspension while cooling with an ice bath. The clear yellow solution was stirred at room temperature overnight, then treated with 100 ml of sat. Na2SO3 solution and 30 ml of 1N HCl and stirred for a further 1 hour. The resulting suspension was treated with 150 ml of water and the solution was evaporated on a rotary evaporator in order to remove the majority of the methanol. The precipitated yellow crystals were filtered off under suction, taken up in CH2Cl2, the solution was dried over MgSO4, filtered and evaporated. The residue was dissolved in 450 ml of hot ethyl acetate and the solution was treated with 450 ml of hexane. After standing overnight the crystallizate was filtered off under suction, washed with a small amount of hexane and dried at 0.1 mbar. There were obtained 54 g of (3,4-dimethoxyphenyl)diphenylphosphine oxide as a light beige powder. M.p. 154.5°-156° C.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringstirred for a further 1 hour
  3. customthe solution was evaporated on a rotary evaporator in order
  4. customto remove the majority of the methanol
  5. filtrationThe precipitated yellow crystals were filtered off under suction
  6. dry with materialthe solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residue was dissolved in 450 ml of hot ethyl acetate
  10. additionthe solution was treated with 450 ml of hexane
  11. waitAfter standing overnight
  12. filtrationthe crystallizate was filtered off under suction
  13. washwashed with a small amount of hexane
  14. customdried at 0.1 mbar

Sources & evidence

ORD record
ord-29b478fb430d4c20b9618471bad937fe
Source dataset
uspto-grants-1996_01
Patent number
US05488172

Reaction notes

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