p-Toluenesulfonic acid → HCID 12040567, compound

HRID 1836932Notes

Reaction equation

HRID 1836932 reaction equation
[CH3:1][Si:2]([O:15][CH:16](C)C)([O:11][CH:12](C)C)[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][Si:2]([O:11][CH3:12])([O:15][CH3:16])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH2:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12040568HCID 12040568, compound

Product 1

HCID 12040567HCID 12040567, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 4-(methyldiisopropyloxysilyl)styrene (8.23 g, 31 mmol) was dissolved in dry methanol (10 ml,). 1% molar of p-toluene sulfonic acid (17 mg) was added all at once. The yellow suspension was stirred for 4 hours. The organic solvent was pumped off and the corresponding crude oil was distilled under vacuum (B.p. 70-80° C., 5.10−2 mbar) to afford 4-(methyldimethoxysilyl)styrene as a yellow oil (4 g, 20 mmol) in 65% yield. 1H NMR (CDCl3, δ, ppm) 7.64 (2H, d); 7.49 (2H, d); 6.77 (1H, dd), 5.84 (1H, d), 5.33 (1H, d), 3.60 (6H, s); 0.39 (3H, s).

Workup

  1. distillationthe corresponding crude oil was distilled under vacuum (B.p. 70-80° C., 5.10−2 mbar)

Sources & evidence

ORD record
ord-ab4d659a04bf4de9a02a53d8cd642f3e
Source dataset
uspto-grants-2004_08
Patent number
US06780471B2

Reaction notes

Loading…