Tetraethoxysilane → Cyclohexyl(triethoxy)silane

HRID 1424699Notes

Reaction equation

HRID 1424699 reaction equation
C(O[Si:4]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.[CH:14]1([Mg]Cl)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[Cl-].[NH4+]>C(OCC)C>[CH:14]1([Si:4]([O:5][CH2:6][CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6517TetraethoxysilaneHCID 25517Ammonium ChlorideHCID 178478990HCID 178478990, compound

Product 1

HCID 15653995Cyclohexyl(triethoxy)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

60 ml of dry diethyl ether and 14.0 gram (0.067 mole) of tetraethoxysilane were charged in a 250 ml flask equipped with a reflux condenser and a stirring apparatus in an atmosphere of nitrogen and above prepared solution of cyclohexyl magnesium chloride was slowly added while keeping the internal temperature below 10° C. After completion of addition stirring was carried out at room temperature for 6 hours and at reflux temperature for 2 hours. To the resulting reaction mass 10-20 ml of saturated aqueous ammonium chloride solution was added drop wise to dissolve magnesium salt. The organic layer was separated from the aqueous layer, dried and evaporated to give crude cyclohexyltriethoxysilane. This crude was purified by fractional distillation under reduced pressure, yielding 14.2 gram of pure cyclohexyltriethoxysilane (86% of the theoretical maximum yield based on the amount of tetraethoxysilane).

Workup

  1. customequipped with a reflux condenser
  2. additionwas slowly added
  3. customthe internal temperature below 10° C
  4. additionAfter completion of addition
  5. temperatureat reflux temperature for 2 hours
  6. additionwas added drop wise
  7. customThe organic layer was separated from the aqueous layer
  8. customdried
  9. customevaporated
  10. customto give crude cyclohexyltriethoxysilane
  11. distillationThis crude was purified by fractional distillation under reduced pressure

Sources & evidence

ORD record
ord-f2fc33d0091343b082a48a7dae3113b9
Source dataset
uspto-grants-2015_01
Patent number
US08927753B2

Reaction notes

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