Allyl methacrylate → 2-Propenoic acid-3-(1,1,3,3-tetramethyldisiloxanyl)propyl ester

HRID 887959Notes

Reaction equation

HRID 887959 reaction equation
[CH3:1][SiH2:2][O:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[C:8]([O:13][CH2:14][CH:15]=C)(=[O:12])[C:9](C)=[CH2:10].[CH:17]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>>[CH3:5][Si:4]([CH2:7][CH2:15][CH2:14][O:13][C:8](=[O:12])[CH:9]=[CH2:10])([CH3:6])[O:3][SiH:2]([CH3:17])[CH3:1]

Participants

4

Reactant 3

HCID 7274Allyl methacrylateHCID 11776TriphenylphosphineHCID 57376941Tetramethyl disiloxane

Product 1

HCID 157113442-Propenoic acid-3-(1,1,3,3-tetramethyldisiloxanyl)propyl ester

Procedure

Into a 1000 mL round bottom flask, equipped with a Teflon-coated stir bar and located in a water bath at room temperature, is added tetramethyidisiloxane (134 grams, 1 mole) and allyl methacrylate (126 grams, 1 mole). A reaction is initiated by the addition of Karstedt's catalyst (0.5 mL) and the charge is stirred for 3 hours. At this point PPh3 (10 mL) is added and the charge is vacuum distilled (0.1 millibar) at 50° C. The product, 112 grams of colorless liquid, is rectified on a spinning band column (75 plates, 0.3 mbar) to yield 41 grams (16%) of SiH-MA. The boiling point is determined to be 62° C.

Workup

  1. customInto a 1000 mL round bottom flask, equipped with a Teflon-coated stir bar
  2. customlocated in a water bath at room temperature
  3. distillationdistilled (0.1 millibar) at 50° C
  4. customto yield 41 grams (16%) of SiH-MA
  5. customto be 62° C.

Sources & evidence

ORD record
ord-646a4057c8ba44a5b44d2895b3eb9318
Source dataset
uspto-grants-2012_08
Patent number
US08247515B2

Reaction notes

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