Hydrochloric Acid → tert-Butyldimethylsilyl chloride

HRID 256747Notes

Reaction equation

HRID 256747 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][Si:6]([CH3:16])([CH3:15])O[Si:8]([CH3:14])([CH3:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[ClH:17]>>[C:9]([Si:8]([CH3:14])([CH3:13])[Cl:17])([CH3:12])([CH3:11])[CH3:10].[CH3:5][Si:6]([CH3:16])([CH3:15])[Cl:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl Chloride2×HCID 5900171-tert-Butyl-1,1,3,3,3-pentamethyldisiloxane

Product 2

HCID 6397ChlorotrimethylsilaneYield 79%HCID 28928tert-Butyldimethylsilyl chlorideYield 83.2%

Procedure

The reaction system was stirred at room temperature while dropwise adding thionyl chloride through the dropping funnel. In this manner, pentamethyl-t-butyl-disiloxane was reacted with thionyl chloride while dropwise adding the latter and supplying hydrogen chloride gas to the reaction solution. After stirring the reaction solution over 4 hours, it was distilled at 125° C. to give 31.3 g (yield 83.2%) of t-butyldimethylchlorosilane and 21.4 g (yield 79.0%) of trimethylchlorosilane. There was not observed the formation of any viscous oily substance, the distillation temperature during the purification could substantially be decreased and the post-treatment of the reaction vessel was very easy.

Workup

  1. additionwhile dropwise adding the latter
  2. distillationit was distilled at 125° C.

Sources & evidence

ORD record
ord-4b27e93ff6fa47f3bf30ac2d431ceea1
Source dataset
uspto-grants-1993_11
Patent number
US05258537

Reaction notes

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