1-Dodecene → Dichlorodidodecylsilane

HRID 1797765Notes

Reaction equation

[Cl:1][SiH2:2][Cl:3].[CH2:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]>C(O)(C)C.O.Cl.Cl.Cl[Pt](Cl)(Cl)Cl>[Cl:1][Si:2]([Cl:3])([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a dry tarred 500 mL Schlenk bomb flask was condensed 29.0 g (0.286 mol) of dichlorosilane at −78° C. To this was added 100 g (0.594 mol) of 1-dodecene under an argon flow. This mixture was allowed to warm to 0° C., then 100 mg (0.193 mmol) of hexachloroplatinic acid hexahydrate dissolved in 2 mL of isopropanol was added via syringe. The mixture was allowed to slowly warm to room temperature where it was allowed to stir for 40 hours. After this time the solution was cannula transferred into a dry 250 mL 3-necked round bottom flask equipped with a fractional distillation apparatus. The mixture was distilled at 220° C. at 0.1 mmHg. Yield: 78.1 g (62.5%). 1H NMR (400 MHz, C6D6): δ=1.6-1.4 (m, 4H), 1.4-1.1 (m, 36H), 1.0-0.8 (m, 10H). 13C NMR (100 MHz, C6D6): δ=33.19, 32.72, 30.51, 30.30, 30.21, 29.89, 23.51, 23.16, 20.92, 14.77. HRMS (EI) m/z, calcd for C24H50Cl2Si (M+): 436.3059; found: 436.3058.

Workup

customTo a dry tarred 500 mL Schlenk bomb flask was
additionwas added via syringe
temperatureto slowly warm to room temperature where it
customtransferred into a dry 250 mL 3-necked round bottom flask
customequipped with a fractional distillation apparatus
distillationThe mixture was distilled at 220° C. at 0.1 mmHg

Sources & evidence

ORD record: ord-a479cd8cd4bf40a4823c0309ae2e79a7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343382B2

Reaction notes

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