Methyl Acrylate → (CH3O)3Si(CH2)2S(CH2)2COOCH3
Reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[Si:7]([CH2:14][CH2:15][SH:16])([O:12][CH3:13])([O:10][CH3:11])[O:8][CH3:9].[OH-].[K+]>O>[Si:7]([CH2:14][CH2:15][S:16][CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])([O:12][CH3:13])([O:10][CH3:11])[O:8][CH3:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 26 gms of methyl acrylate (0.3 mols) and 36.4 gms of (CH3O)3SiCH2CH2SH was catalyzed by adding 1 ml. of N/2 alcoholic KOH into a 250 ml., round bottomed glass flask, with stirring. An exothermic reaction raised the temperature to 60° C. The mixture was refluxed for 30 minutes and then distilled under vacuum to recover 46 gms of water-white product with a boiling point at 0.7 mm Hg pressure of 115°-125° C. for an 87 percent yield of (CH3O)3Si(CH2)2S(CH2)2COOCH3. d420 =1.115, ND25 =1.4546. One tenth gram mol (26.8 gms) of this product was saponified by refluxing for one hour with 4 grams of NaOH (0.1 mol) in 80 gms of H2O. Methanol and other volatiles were taken off until the temperature, with auxiliary heating, reached 100° C. The residue was diluted to 100 gms with water to give a 1 molal solution of (Na)O1.5 Si(CH2)2S(CH2)2COONa.
Workup
- additionby adding 1 ml
- customAn exothermic reaction
- temperatureThe mixture was refluxed for 30 minutes
- distillationdistilled under vacuum
Sources & evidence
- ORD record
- ord-3a367d418dfa460ca0640db1fb5662f0
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04344860
Reaction notes
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