Allyl acetate → HCID 20479601, compound

HRID 1390530Notes

Reaction equation

HRID 1390530 reaction equation
[CH3:1][SiH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O:18][CH2:19][CH:20]=[CH2:21])(=O)C>C(O)(C)C.[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[OH:18][CH2:19][CH2:20][CH2:21][Si:2]([CH3:1])([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 11584Allyl acetateHCID 69893Benzene, 1,1'-(methylsilylene)bis-2×

Product 1

HCID 20479601HCID 20479601, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 61859Chloroplatinic acidCatalyst2×HCID 3776IsopropanolSolvent

Procedure

Methyldiphenylsilane (100 g, 0.49 mol) was added at 90° over a period of 4 hrs, with stirring, to a mixture of 100 g (1.0 mol) of allyl acetate and 0.10 ml of a 0.1 M chloroplatinic acid solution in isopropanol. When half of the methyldiphenylsilane was added an additional 0.10 ml of the chloroplatinic acid solution was added. Excess allyl acetate was distilled 15 min. after the addition was completed. The residue was dissolved in 150 ml of methanol and a solution of 20 g of sodium hydroxide in 40 ml of water was added dropwise. After the mixture was stirred for 2 hrs, 200 ml of water was added, and the mixture was neutralized with hydrochloric acid. The product was extracted with methylene chloride, dried over magnesium sulfate and distilled to give 65 g (50%) of (3-hydroxypropyl) methyldiphenylsilane, bp 130°-140° (0.03 to 0.07 mm). p-Toluenesulfonyl chloride 3.5 g, 0.184 mol) was added to a solution of 29 g (0.118 mol) of (3-hydroxypropyl)methyldiphenylsilane and 14.6 g (0.184 mol) of pyridine in 60 ml of methylene chloride at 0°. The mixture was kept at 0°-5° for 18 hrs and 40 ml of ice water was added. The water layer was extracted with 40 ml of methylene chloride, and the combined organic layers were washed with 2-30 ml portions of water. Solvent was removed and the product was crystallized from ether to give 46 g (95%) (3-propyl)methyldiphenyl p-toluenesulfonate, mp 68°-69°.

Workup

  1. additionwas added
  2. distillationExcess allyl acetate was distilled 15 min.
  3. additionafter the addition
  4. dissolutionThe residue was dissolved in 150 ml of methanol
  5. additiona solution of 20 g of sodium hydroxide in 40 ml of water was added dropwise
  6. addition200 ml of water was added
  7. extractionThe product was extracted with methylene chloride
  8. dry with materialdried over magnesium sulfate
  9. distillationdistilled

Sources & evidence

ORD record
ord-010c4008e7464a8baa4d4da5d4886613
Source dataset
uspto-grants-1979_02
Patent number
US04139403

Reaction notes

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