Isopropanol → 1-(2-Methylphenethyl)-3-vinyltetramethyldisiloxane

HRID 1463521Notes

Reaction equation

HRID 1463521 reaction equation
CC([C:4]1[CH:9]=CC=CC=1)=C.[CH3:10][SiH:11]([CH3:13])Cl.[CH3:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])Cl.CC(C)=C[SiH2]Cl.C([OH:36])(C)C>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.O>[CH3:14][C:15]1[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=1[CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[O:36][Si:11]([CH3:13])([CH3:10])[CH:9]=[CH2:4]

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 7407Alpha-MethylstyreneHCID 66108ChlorodimethylsilaneHCID 190907002-MethylphenethyldimethylchlorosilaneHCID 57370515C4H9ClSi

Product 1

HCID 190907021-(2-Methylphenethyl)-3-vinyltetramethyldisiloxane

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The following were charged to a 1 L roundbottom flask equipped with a stirrer, thermometer, and addition funnel and heated to 70° C.: 375 g (3.15 mol) alpha-methylstyrene and 0.6 mL 1% isopropanolic chloroplatinic acid solution. 285 g (3.0 mol) dimethylchlorosilane was then dripped in from the addition funnel over 1 hour. The reaction was subsequently maintained at 80° C. for 1 hour and cooled. 212 g (1.0 mol) of the 2-methylphenethyldimethylchlorosilane product and 217 g (1.8 mol) dimethylvinylchlorosilane were dripped into a mixture of 300 g water and 100 g isopropyl alcohol. The resulting hydrolyzate was washed with water 3 times, the water (lower) layer was removed, and heating in vacuo produced 180 g (65% of the theoretical yield) 1-(2-methylphenethyl)-3-vinyltetramethyldisiloxane . This 1-(2-methylphenethyl)-3-vinyltetramethyldisiloxane had a refractive index of 1.471, a viscosity of 2.2 centistokes, and a boiling point of 121° C./5 mmHg.

Workup

  1. additionThe following were charged to a 1 L roundbottom flask
  2. customequipped with a stirrer
  3. additionthermometer, and addition funnel
  4. temperatureThe reaction was subsequently maintained at 80° C. for 1 hour
  5. temperaturecooled
  6. washThe resulting hydrolyzate was washed with water 3 times
  7. customthe water (lower) layer was removed
  8. temperatureheating in vacuo
  9. customproduced 180 g (65% of the

Sources & evidence

ORD record
ord-f5f59dbc12d3470098adb30ed5acacf7
Source dataset
uspto-grants-1994_04
Patent number
US05300669

Reaction notes

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