Ethanol → 1-Methylimidazole

HRID 898071Notes

Reaction equation

HRID 898071 reaction equation
[Si](Cl)(Cl)(Cl)Cl.C(O)C.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CCCCCCC>[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[CH3:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

6

Reactant 3

HCID 702EthanolHCID 13901-MethylimidazoleHCID 24816Silicon tetrachloride

Product 2

HCID 13901-MethylimidazoleHCID 67804438HCID 67804438, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

SiCl4 (50.0 g, 0.294 mol) is slowly added with icebath cooling and under an N2 atmosphere at a temperature of 10-15° C. to a solution of ethanol (54.3 g, 1.17 mol) and 1-methylimidazole (MIA, 98.9 g, 1.21 mol) in heptane (400 ml). The reaction mixture is stirred overnight and the phases are separated. 142.9 g of MIA hydrochloride are obtained as a colorless solid (theory: 141.9 g of MIA+MIA.HCl). The organic phase is cautiously concentrated, in order to keep losses of volatile product low. 48.1 g of tetraethoxysilane (theory: 61.3 g) are obtained as a slightly cloudy, colorless oil having a purity of 91.1% (GC).

Workup

  1. customthe phases are separated

Sources & evidence

ORD record
ord-5eeb6a6edc714fdf84c98839bd37bc25
Source dataset
uspto-grants-2008_04
Patent number
US07351339B2

Reaction notes

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