Sodium Hydroxide → p-Phenylenebis(dimethylsilanol)

HRID 634871Notes

Reaction equation

HRID 634871 reaction equation
[CH3:1][SiH:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([SiH:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=1.[H][H].[OH-:15].[Na+].[OH:17]P([O-])(O)=O.[K+]>O.CO>[OH:15][Si:9]([CH3:11])([CH3:10])[C:6]1[CH:7]=[CH:8][C:3]([Si:2]([OH:17])([CH3:12])[CH3:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 75601(4-Dimethylsilylphenyl)-dimethyl-silaneHCID 516951Monobasic potassium phosphateHCID 178418361HCID 178418361, compound

Product 1

HCID 75989p-Phenylenebis(dimethylsilanol)Yield 771.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

Into a flame dried 250 mL three neck round bottom flask equipped with magnetic stirrer and water condenser was added anhydrous ethanol (122 mL) and a small piece of sodium metal under argon. The ethanol was heated to reflux. Then, the 1,4-bis(dimethylsilyl)benzene (100 g, 51.5 mmol) was added dropwise to the reaction flask with stirring over 30 minutes. When hydrogen evolution ceased, the reaction mixture was added with vigorous stirring to a mixture of NaOH (69.45 g), CH3OH (427 mL) and H2O (48.8 mL). After standing for 15 min, another solution of NaOH (69.45 g) in H2O (463.6 mL) was added to the mixture. The mixture was allowed to stand for 30 minutes with occasional shaking and then poured into a vigorously stirred solution of KH2PO4 (610 g) in excess ice and H2O (2440 mL). Crude disilanol product was precipitated as a white solid, filtered, dissolved in ethyl ether (610 mL), and washed with an equal volume of water. The ether solution of the product was dried (anhydrous Na2SO4) and concentrated to give a white solid. The solid was recrystallized from hot CCl4 (500 mL) and dried at 60° C. overnight in vacuo to provide final needle-like white solid product (90 g, yield 77.6%). 1H and 13C NMR analyses were consistent with the structure assigned.

Workup

  1. dry with materialInto a flame dried 250 mL three neck round bottom flask
  2. customequipped with magnetic stirrer and water condenser
  3. additionwas added anhydrous ethanol (122 mL)
  4. temperatureThe ethanol was heated to reflux
  5. additionthe reaction mixture was added
  6. waitAfter standing for 15 min
  7. waitto stand for 30 minutes
  8. stirringwith occasional shaking
  9. customCrude disilanol product was precipitated as a white solid
  10. filtrationfiltered
  11. dissolutiondissolved in ethyl ether (610 mL)
  12. washwashed with an equal volume of water
  13. dry with materialThe ether solution of the product was dried (anhydrous Na2SO4)
  14. concentrationconcentrated
  15. customto give a white solid
  16. customThe solid was recrystallized from hot CCl4 (500 mL)
  17. customdried at 60° C. overnight in vacuo

Sources & evidence

ORD record
ord-124ee2fd44c845498373cedf74f64b0e
Source dataset
uspto-grants-2001_02
Patent number
US06184269B2

Reaction notes

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