Quinone → 2-Propenoic acid, 2-methyl-, 3-(chlorodimethylsilyl)propyl ester

HRID 622328Notes

Reaction equation

HRID 622328 reaction equation
C1(=O)C=CC(=O)C=C1.[Cl:9][SiH:10]([CH3:12])[CH3:11].[C:13]([O:18][CH2:19][CH:20]=[CH2:21])(=[O:17])[C:14]([CH3:16])=[CH2:15]>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[C:13]([O:18][CH2:19][CH:20]=[CH2:21])(=[O:17])[C:14]([CH3:16])=[CH2:15].[C:13]([O:18][CH2:19][CH2:20][CH2:21][Si:10]([Cl:9])([CH3:12])[CH3:11])(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

6

Reactant 3

HCID 4650QuinoneHCID 7274Allyl methacrylateHCID 66108Chlorodimethylsilane2×

Product 2

HCID 7274Allyl methacrylateHCID 27595272-Propenoic acid, 2-methyl-, 3-(chlorodimethylsilyl)propyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 61859Chloroplatinic acidCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 40 milligrams of hexachloroplatinic acid and 1.0 gram of benzoquinone in 25 grams of allyl methacrylate was heated under anhydrous conditions in an oil bath to 60° C. Chlorodimethylsilane (24 milliliters) was then added slowly by a syringe. The hydrosilylation reaction was exothermic and the chlorodimethylsilane was added at a rate to maintain the temperature of the reaction between 58° C. and 62° C. Distillation of the reaction mixture afforded 4.8 grams of allyl methacrylate and 28.6 grams (81 percent yield based on recoverd starting material) of 3-(chlorodimethylsilyl)propyl methacrylate (bp 82° to 83° C. 0.5τ). This product was characterized by 1H NMR (CDCl3) δ0.34, s, 6H, SiCH3 ; 0.61 to 0.89, m, 2H CH2Si; 1.58 to 1.91, m, 5H, CH2CH3 ; 3.89 to 4.13, t, 2H, CH2 ; 5.52 to 5.35, t, 1H, vinylic; 5.89 to 6.07, t, 1H, vinylic.

Workup

  1. customThe hydrosilylation reaction
  2. temperatureto maintain
  3. customthe temperature of the reaction between 58° C. and 62° C
  4. distillationDistillation of the reaction mixture

Sources & evidence

ORD record
ord-14964ae9c3a744f3867f714b11e40e2c
Source dataset
uspto-grants-1988_09
Patent number
US04770968

Reaction notes

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