p-Toluenesulfonic acid → HCID 12070525, compound

HRID 1059044Notes

Reaction equation

HRID 1059044 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].CO[CH:8](OC)[CH2:9][CH2:10][Si:11]([O:16][CH3:17])([O:14][CH3:15])[O:12][CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:13][O:12][Si:11]([O:16][CH3:17])([O:14][CH3:15])[CH2:10][CH2:9][CH:8]1[S:5][CH2:1][CH2:2][CH2:3][S:4]1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80131,3-PropanedithiolHCID 11333580HCID 11333580, compound

Product 1

HCID 12070525HCID 12070525, compound

Procedure

The procedure and apparatus of Example 1 were used with 22.4 g (0.207 m) of propane-1,3-dithiol, 46.4 g (0.207 m) of (3,3-dimethoxypropyl)trimethoxysilane, 0.14 g of p-toluenesulfonic acid, and 100 ml of xylenes solvent. Methanol was removed by distillation as the contents of the flask were heated at reflux (143°) for 2 hours. The crude product, excluding solvent, contained 75% of the title product and 7.4% of the monosubstituted product, (MeO)3Si(CH2)2CH(OMe)S(CH2)3SH, as determined by GC/MS.

Workup

  1. customMethanol was removed by distillation as the contents of the flask
  2. temperaturewere heated
  3. temperatureat reflux (143°) for 2 hours

Sources & evidence

ORD record
ord-deb939b539874f80b01c98ebc26e7b29
Source dataset
uspto-grants-2003_02
Patent number
US06518335B2

Reaction notes

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