Chlorosulfonic acid → [4-(Chlorosulfonyl)phenethyl] methyl allylchlorosilane
Reaction equation
[CH2:1]([CH2:9][SiH](Cl)Cl)[CH2:2]C1C=CC=CC=1.ClS(O)(=O)=O.[Cl:18][S:19]([C:22]1[CH:33]=[CH:32][C:25]([CH2:26][CH2:27][CH2:28][SiH:29]([Cl:31])Cl)=[CH:24][CH:23]=1)(=[O:21])=[O:20].C([Mg]Cl)C=C>>[Cl:18][S:19]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][CH2:27][CH2:28][SiH:29]([CH2:9][CH:1]=[CH2:2])[Cl:31])=[CH:32][CH:33]=1)(=[O:20])=[O:21]Participants
Procedure
Phenethylmethyldichlorosilane (Gelest, Inc., Tullytown, Pa., USA) is chlorosulfonated with chlorosulfonic acid as described in Chem. Abstr. 103 P71494v. This yields [4-(chlorosulfonyl)phenethyl] methyldichlorosilane which is reacted with allyl-magnesium chloride to form [4-(chlorosulfonyl)phenethyl] methyl allylchlorosilane. This product is reacted with octadecyl methylchlorosilane (boiling point of 175° to 177°/0.5 mm, from reaction of octadecylmagnesium bromide with methyldichlorosilane) under chloroplatinic acid catalysis to form 1-(octadecyl methylchlorosilyl)-3-{methyl [4-(chlorosulfonyl)phenethyl] chlorosilyl}propane. This material is reacted with dimethylamine to form 1-(octadecyl methyl dimethylaminosilyl)-3-{methyl [4-(chlorosulfonyl)-phenethyl] dimethylaminosilyl}propane.
Sources & evidence
- ORD record
- ord-52a85313fa8f4116b1e3aa1407595192
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05869724
Reaction notes
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