(3-Chloropropyl)triethoxysilane → Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

HRID 491007Notes

Reaction equation

HRID 491007 reaction equation
[C:1]([O-:10])(=[S:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Na+].Cl[CH2:13][CH2:14][CH2:15][Si:16]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19]>>[C:1]([S:9][CH2:13][CH2:14][CH2:15][Si:16]([O:17][CH2:18][CH3:19])([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 78771(3-Chloropropyl)triethoxysilaneHCID 24940094Sodium thiooctanoate

Product 1

HCID 12135713Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

Conditions

Temperature
90 °C

Procedure

The aqueous solution of sodium thiooctanoate was heated to 40° C. and 11 grams of 34.5% HEGCl solution were added. Also, about 296 grams of 3-chloro-1-propyltriethoxysilane were added batch-wise to the reaction mixture. The product was heated further to 90° C. and stirred for 5 hours. At this point, agitation was discontinued and the two-phase system was allowed to separate. The bottom aqueous phase was removed and the top crude product was recovered. The crude layer was purified by stripping the material at 135-145° C. and 5-10 mm Hg. The process yielded about 251 grams of pale yellow and clear product with a typical GC purity of 92-94%.

Workup

  1. addition11 grams of 34.5% HEGCl solution were added
  2. customto separate
  3. customThe bottom aqueous phase was removed
  4. customthe top crude product was recovered
  5. customThe crude layer was purified
  6. customat 135-145° C.
  7. customThe process yielded about 251 grams of pale yellow and clear product with a typical GC purity of 92-94%

Sources & evidence

ORD record
ord-882e0457271943b4a5b7e927319cb476
Source dataset
uspto-grants-2009_05
Patent number
US07528273B2

Reaction notes

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