3-(Trimethoxysilyl)propyl chloride → 3-(Trimethoxysilyl)propyl methacrylate
Reaction equation
[C:1]([O-:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[K+].Cl[CH2:9][CH2:10][CH2:11][Si:12]([O:17][CH3:18])([O:15][CH3:16])[O:13][CH3:14]>[Cl-].CO[Si](OC)(OC)CCC[N+]1C=CC(N(C)C)=CC=1>[C:1]([O:6][CH2:9][CH2:10][CH2:11][Si:12]([O:17][CH3:18])([O:15][CH3:16])[O:13][CH3:14])(=[O:5])[C:2]([CH3:4])=[CH2:3]Participants
Conditions
- Temperature
- 135 °C
Procedure
124 g (1 mol) of potassium methacrylate were admixed with 198.5 g (1 mol) of 3-chloropropyltrimethoxysilane, 2.7 g of 1-(3'-trimethoxysilylpropyl)-4-dimethylaminopyridinium chloride and 0.5 g of N,N'-diphenyl-p-phenylamine, and the mixture was heated to 135° C. while stirring. After 1 hour at this temperature the mixture was cooled and the potassium chloride which had precipitated was filtered off and washed with 60 g of methanol. The methanol was evaporated from the combined filtrates, and the residue was distilled under reduced pressure. 225 g of 3-methacryloxypropyltrimethoxysilane having a boiling point of 82° C. (0.4 mbar) were obtained. The yield was 90.7% of theory, based on the amount of potassium methacrylate which was used. The purity of the product was 99.0%. In the gas chromatogram only traces of 4-dimethylaminopyrrdine were detectable. A 2% solution of the product in water with a pH of 4 contained no oily separation of any kind.
Workup
- temperatureAfter 1 hour at this temperature the mixture was cooled
- customthe potassium chloride which had precipitated
- filtrationwas filtered off
- washwashed with 60 g of methanol
- customThe methanol was evaporated from the combined filtrates
- distillationthe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-d37ddc4a9ca144bfa99bfa68e7ea946f
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05117027
Reaction notes
Loading…