Isopropanol → 2-Methylphenethylpentamethyldisiloxane

HRID 1463522Notes

Reaction equation

HRID 1463522 reaction equation
CC(C1C=CC=CC=1)=C.C[SiH](C)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.[CH3:27][Si:28]([CH3:31])([CH3:30])Cl.C([OH:35])(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:35][Si:28]([CH3:31])([CH3:30])[CH3:27]

Participants

8

Reactant 5

HCID 3776IsopropanolHCID 6397ChlorotrimethylsilaneHCID 7407Alpha-MethylstyreneHCID 66108ChlorodimethylsilaneHCID 190907002-Methylphenethyldimethylchlorosilane

Product 1

HCID 190907032-Methylphenethylpentamethyldisiloxane

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 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 196 g (1.8 mol) trimethylchlorosilane were dripped into a mixture of 300 g water and 100 g isopropyl alcohol. The resulting reaction mixture was washed with water 3 times, the water (lower) layer was removed, and the reaction mixture (upper layer) was heated in vacuo to give 190 g (71% of the theoretical yield) 2-methylphenethylpentamethyldisiloxane. This 2-methylphenethylpentamethyldisiloxane had a refractive index of 1.463. a viscosity of 2.1 centistokes, and a boiling point of 120° C./10 mmHg.

Workup

  1. additionThe following were charged to a 1 L roundbottom flask
  2. customequipped with stirrer
  3. additionthermometer, and addition funnel
  4. temperatureThe reaction was subsequently maintained at 80° C. for 1 hour
  5. temperaturecooled
  6. customThe resulting reaction mixture
  7. washwas washed with water 3 times
  8. customthe water (lower) layer was removed
  9. temperaturethe reaction mixture (upper layer) was heated in vacuo
  10. customto give 190 g (71% of the

Sources & evidence

ORD record
ord-6c605282cbe4408a98580e49a63cab8b
Source dataset
uspto-grants-1994_04
Patent number
US05300669

Reaction notes

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