1,6-Dichlorohexane → (CH3CH2O)3Si(CH2)3S(CH2)6Cl
Reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Cl:8].[SH:9][CH2:10][CH2:11][CH2:12][Si:13]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].CC[O-].[Na+]>>[Si:13]([CH2:12][CH2:11][CH2:10][S:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Cl:8])([O:17][CH2:18][CH3:19])([O:20][CH2:21][CH3:22])[O:14][CH2:15][CH3:16]Participants
Conditions
- Temperature
- 80 °C
Procedure
A 1-liter separable flask equipped with a nitrogen gas inlet, thermometer, Dimroth condenser and dropping funnel was charged with 310.0 g (2.0 mol) of 1,6-dichlorohexane and heated at 80° C. With stirring, the reaction product of 3-mercaptopropyltriethoxysilane with sodium ethylate was slowly added dropwise. After the completion of dropwise addition, the solution was continuously stirred at 80° C. for 5 hours, and then cooled. From the solution, the salt was filtered off and the ethanol and excess 1,6-dichlorohexane were distilled off in vacuum. The residual solution was subjected to vacuum distillation, collecting 64.2 g of a colorless clear liquid at a boiling point of 148–150° C./0.005 Torr. On analysis by IR, 1H-NMR and MS, the liquid was identified to be a compound of the following formula. (CH3CH2O)3Si(CH2)3S(CH2)6Cl Analysis by gas chromatography gave a purity of 98.7%.
Workup
- customA 1-liter separable flask equipped with a nitrogen gas inlet
- additionAfter the completion of dropwise addition
- stirringthe solution was continuously stirred at 80° C. for 5 hours
- temperaturecooled
- filtrationFrom the solution, the salt was filtered off
- distillationthe ethanol and excess 1,6-dichlorohexane were distilled off in vacuum
- distillationThe residual solution was subjected to vacuum distillation
- customcollecting 64.2 g of a colorless clear liquid at a boiling point of 148–150° C./0.005 Torr
Sources & evidence
- ORD record
- ord-c572434c217843b9a49e0c9ff37977b2
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166735B2
Reaction notes
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