Silicon tetrachloride → p-Methoxybenzyltrichlorosilane

HRID 1252742Notes

Reaction equation

HRID 1252742 reaction equation
[Mg].[Si:2]([Cl:6])(Cl)([Cl:4])[Cl:3].[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Cl)=[CH:11][CH:10]=1>C(OCC)C>[CH3:7][O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][Si:2]([Cl:6])([Cl:4])[Cl:3])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 24816Silicon tetrachlorideHCID 699934-Methyloxybenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 11482253p-MethoxybenzyltrichlorosilaneYield 26.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In a 2-liter three-neck flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer were placed 30 g (1.2 gram atom) of magnesium powder, 170 g (1.00 mol) of silicon tetrachloride, and 500 ml of diethyl ether. The flask was cooled below 10° C. A mixture of 100.0 g (0.639 mol) of p-methoxybenzyl chloride and 200 ml of diethyl ether was added dropwise with stirring for the dropping funnel over 4 hours. After aging at room temperature for 1 hour, excess magnesium and magnesium chloride were removed by suction filtration. The filtrate was distilled to give 44.0 g (0.172 mol) of the desired product in a yield of 26.9%.

Workup

  1. customIn a 2-liter three-neck flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperatureThe flask was cooled below 10° C
  4. additionwas added dropwise
  5. waitAfter aging at room temperature for 1 hour
  6. customexcess magnesium and magnesium chloride were removed by suction filtration
  7. distillationThe filtrate was distilled

Sources & evidence

ORD record
ord-484ad3e8dc99417887e965ab527d8103
Source dataset
uspto-grants-1988_05
Patent number
US04745169

Reaction notes

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