Hydrochloric Acid → HCID 13708490, compound

HRID 2231761Notes

Reaction equation

HRID 2231761 reaction equation
[C:1]1([CH3:7])C=CC=CC=1.[Na].[Si:9](Cl)([CH3:12])([CH3:11])[CH3:10].Cl>COCCOCCOC.O>[Si:9]([CH2:7][CH:1]([Si:9]([CH3:12])([CH3:11])[CH3:10])[Si:9]([CH3:12])([CH3:11])[CH3:10])([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 5360545Sodium

Product 1

HCID 13708490HCID 13708490, compoundYield 7.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent3×

Conditions

Temperature
115 °C

Procedure

In a 500 ml three-necked standard taper joint round-bottomed flask were combined 12.2 g (0.53 mol) of Na metal chunks and 201.8 g of anhydrous diglyme. Flask was fitted with an electric heating mantle, mechanical stirrer (stainless steel blade), addition funnel, Dewar condenser (containing toluene cooled by immersion coil through which ice water was circulated), thermometer, and valves to maintain an inert atmosphere (nitrogen). Heat was applied, melting the sodium, and addition of a mixture of 54.8 g (0.5 mol) of Me3SiCl and 24.3 g (0.24 mol) of CH2 =CHSiMe3 begun at 115°, and continued, with continuous heating, at a rate which maintained the reflux temperature above 98°. Heating at reflux (115° C.) continued for 8 hr, and standing at room temperature for 32 hr, followed by termination by slow addition of a solution of 16.0 g H2O in 57.7 g diglyme and neutralization with 5 g conc HCl in 26.8 g diglyme. Salts were removed by filtration, and the organic layer vacuum distilled, yielding 4.65 g (7.9%) of Me3SiCH2CH(SiMe3)2, identified by VPC/NMR, plus 39.6% of Me3SiOSiMe3 and 6.2% of Me3SiSiMe3.

Workup

  1. customIn a 500 ml three-necked standard taper joint round-bottomed flask were combined
  2. temperaturethermometer, and valves to maintain an inert atmosphere (nitrogen)
  3. temperatureHeat
  4. custombegun at 115°
  5. temperaturemaintained the reflux temperature above 98°
  6. temperatureHeating
  7. waitstanding at room temperature for 32 hr
  8. customSalts were removed by filtration
  9. distillationthe organic layer vacuum distilled

Sources & evidence

ORD record
ord-90c40549b8844436b11561b6f5ae255c
Source dataset
uspto-grants-1988_11
Patent number
US04783516

Reaction notes

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