Toluene → HCID 22401836, compound

HRID 259880

Reaction equation

HRID 259880 reaction equation
[CH2:1]([Si:4]([Cl:7])([Cl:6])[Cl:5])[CH:2]=[CH2:3].[Cl-].[Na+].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Cl-].[Al+3].[Cl-].[Cl-]>[CH3:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:2]([CH3:3])[CH2:1][Si:4]([Cl:7])([Cl:6])[Cl:5]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 5234Sodium ChlorideHCID 7867Trichloro-2-propen-1-ylsilane

Product 1

HCID 22401836HCID 22401836, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6451240Aluminum(III) ChlorideCatalyst

Conditions

Temperature
50 °C

Procedure

In the same apparatus and procedures as EXAMPLE 1, 9.7 g (105 mmol) of toluene and 0.2 g (1.5 mmol) of aluminum chloride were placed. The flask was then immersed in an ice water bath. To the reaction mixture was slowly added dropwise 3.0 g (15 mmol) of allyltrichlorosilane and the solution was stirred for an hour. After confirming that no toluene was left by gas chromatography, 0.48 g (8.0 mmol) of sodium chloride was added to reaction mixture, warmed up to 50° C. and stirred for two hours to deactivate the catalyst. Vacuum distillation of the reaction products gave 16.3 g (bp 74°-76° C./0.6 mmHg) of 3-(methylphenyl)-1,1,1-trichloro-1-silabutane in 71% yield.

Workup

  1. customThe flask was then immersed in an ice water bath
  2. additionwas added to reaction mixture
  3. stirringstirred for two hours
  4. distillationVacuum distillation of the reaction products

Sources & evidence

ORD record
ord-1edb52c4671f4e50b7a5e30a5a3ef92e
Source dataset
uspto-grants-1996_06
Patent number
US05523444

Linked notes

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