Isopropanol → 3-(2'-Trifluoromethyl-3'-chloropropionoxy)propyltriethoxysilane

HRID 2075308Notes

Reaction equation

[CH2:1]([OH:4])[CH:2]=[CH2:3].[F:5][C:6]([F:13])([F:12])[C:7](=[CH2:11])[C:8]([Cl:10])=O.[CH2:14]([O:16][SiH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[CH3:15].C([OH:27])(C)C>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[F:5][C:6]([F:13])([F:12])[CH:7]([CH2:8][Cl:10])[C:11]([O:4][CH2:1][CH2:2][CH2:3][Si:17]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])[O:16][CH2:14][CH3:15])=[O:27]

Participants

Conditions

Temperature: 50 °C

Procedure

12.1 g (0.21 mole) of allyl alcohol were added dropwise at room temperature and in a flow of nitrogen to 30.6 g (0.19 mole) of 2-trifluoromethyl acrylic acid chloride, and after addition of the allyl alcohol was completed, the components were stirred for 8 hours at 50° C. Gas chromatography confirmed formation of allyl 1-chloro-2-trifluoromethylpropionate, and a non-reacted substance was removed by distillation under a reduced pressure. The product was combined with 0.04 g of a 10% isopropanol solution of a chloroplatinic acid, and 32.8 g (0.2 moles) of triethoxysilane were added dropwise at 70° C. Following this, the product was stirred for 2 hours at 100° C., and the reaction mixture was subjected to distillation to produce 25.7 g of 3-(2′-trifluoromethyl-3′-chloropropionoxy)propyltriethoxysilane. The 1H-NMR spectrum of the obtained product is shown in FIG. 1. The yield was 36%, and the boiling point of the obtained compound was 118° C./2 mm Hg.

Workup

customa non-reacted substance was removed by distillation under a reduced pressure
additionwere added dropwise at 70° C
stirringwas stirred for 2 hours at 100° C.
distillationthe reaction mixture was subjected to distillation

Sources & evidence

ORD record: ord-bf143df8b69f440aabf85ff44a391d49
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919642B2

Reaction notes

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