Sulfuric Acid → 4-Ethoxyphenyldimethylsilane

HRID 1656931Notes

Reaction equation

HRID 1656931 reaction equation
[CH3:1][Si:2]([CH3:13])([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1)Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>C(OCC)C>[CH3:1][SiH:2]([CH3:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14014482Chloro(4-ethoxyphenyl)dimethylsilaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 713607484-EthoxyphenyldimethylsilaneYield 67.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 51 g of dimethyl-(4-ethoxyphenyl)-chlorosilane in 100 ml of absolute diethyl ether is added dropwise to a suspension of 2.55 g of lithium aluminum hydride in 30 ml of absolute diethyl ether under nitrogen at 15°-20° C. Stirring is carried out for 1 hour at 20° C., followed by refluxing for 1 hour. The reaction solution is cooled to 20° C. and poured into 200 ml of 2N sulfuric acid. The phases are separated and, after the aqueous phase has been washed several times with diethyl ether, the organic phases are combined and are evaporated down in a rotary evaporator. Distillation of the residue gives 29.0 g of dimethyl-(4-ethoxyphenyl)-silane (bp. 53° C./0.2 mbar).

Workup

  1. temperatureby refluxing for 1 hour
  2. customThe phases are separated
  3. washafter the aqueous phase has been washed several times with diethyl ether
  4. customare evaporated down in a rotary evaporator
  5. distillationDistillation of the residue

Sources & evidence

ORD record
ord-1e89c608670540268dce5e6c3a764830
Source dataset
uspto-grants-1993_10
Patent number
US05256666

Reaction notes

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