Iodine → 3,3,12,12-Tetramethoxy-2,13-dioxa-7,8-dithia-3,12-disilatetradecane

HRID 703239Notes

Reaction equation

HRID 703239 reaction equation
[CH3:1][O-:2].[Na+].[SH:4][CH2:5][CH2:6][CH2:7][Si:8]([O:13][CH3:14])([O:11][CH3:12])[O:9][CH3:10].II>CO>[CH3:12][O:11][Si:8]([O:13][CH3:14])([O:9][CH3:10])[CH2:7][CH2:6][CH2:5][S:4][S:4][CH2:5][CH2:6][CH2:7][Si:8]([O:11][CH3:12])([O:9][CH3:10])[O:2][CH3:1]

Participants

5

Reactant 3

HCID 807Iodine2×HCID 20473(3-Mercaptopropyl)trimethoxysilaneHCID 10942334Sodium Methoxide

Product 1

HCID 37579733,3,12,12-Tetramethoxy-2,13-dioxa-7,8-dithia-3,12-disilatetradecane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methylate in methanol (97.6 g. 0.51 mole) is diluted with methanol (100 ml), and thereto is added γ-mercaptopropyltrimethoxysilane (100 g, 0.51 mole). The temperature of the mixture raises in a certain degree owing to the mixing heat but return to room temperature after about 30 minutes. To the mixture is added in portions iodine (64.6 g. 0.51 mole) with stirring. In view of exothermic reaction, the reaction vessel is cooled with ice water. After completion of the addition of iodine, the brown mixture is allowed to stand at room temperature for 3 hours to give a clean liquid having pale yellow color. The reaction mixture is moved to a flask, and the methanol solvent is distilled off under reduced pressure with a rotary evaporator. The residue containing white crystals and pale yellow liquid is filtered to separate the oily liquid (86.4 g). This liquid is subjected to analyses of IR, H-NMR and UV spectra, and thereby, it is confirmed that the liquid product is bis[γ-(trimethoxysilyl)propyl ]disulfide of the formula:

Workup

  1. temperatureThe temperature of the mixture raises in a certain degree owing to the mixing
  2. temperatureheat
  3. customIn view of exothermic reaction
  4. waitto stand at room temperature for 3 hours
  5. customto give a clean liquid
  6. customThe reaction mixture is moved to a flask
  7. distillationthe methanol solvent is distilled off under reduced pressure with a rotary evaporator
  8. additionThe residue containing white crystals and pale yellow liquid
  9. filtrationis filtered
  10. customto separate the oily liquid (86.4 g)

Sources & evidence

ORD record
ord-400445aa3d004851b2ca328b0ccacddc
Source dataset
uspto-grants-1991_01
Patent number
US04981937

Reaction notes

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