Methyldichlorosilane → 3-(Dichloromethylsilyl)propyl 2-propenoate

HRID 637735

Reaction equation

HRID 637735 reaction equation
[CH2:1]([O:4][C:5](=[O:8])[CH:6]=[CH2:7])[CH:2]=[CH2:3].[CH3:9][SiH:10]([Cl:12])[Cl:11]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:5]([O:4][CH2:1][CH2:2][CH2:3][Si:10]([CH3:9])([Cl:12])[Cl:11])(=[O:8])[CH:6]=[CH2:7]

Participants

5

Reactant 2

HCID 6376Methyldichlorosilane2×HCID 13835Allyl acrylate

Product 1

HCID 99645883-(Dichloromethylsilyl)propyl 2-propenoateYield 68.3%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalyst2×HCID 11776TriphenylphosphineCatalyst

Conditions

Temperature
65 °C

Procedure

To a three-necked flask equipped as in Example 1 there was added 260 grams allylacrylate (2.32 moles), 0.5 grams catalyst prepared in accordance with U.S. Pat. No. 3,814,730 (2.6 weight percent Pt) and 1.04 grams phenothiazine. The mixture was heated with stirring to 65° C. and, using the vent of the condenser, purged with nitrogen. The heat source was then turned off and 237 grams (2.32 moles) CH3SiHCl2 was added dropwise, the temperature of the reaction mass being maintained at about 70° C. Upon completion of the addition of methyldichlorosilane the crude product was cooled to room temperature. One gram phenothiazine and 0.05 gram triphenyl phosphine were added to the product prior to distillation. Acryloxypropylmethyldichlorosilane (360 grams, 68% yield) was distilled at 109°-112° C./10 mm Hg.

Workup

  1. customTo a three-necked flask equipped as in Example 1 there
  2. customprepared in accordance with U.S
  3. temperatureThe mixture was heated
  4. custompurged with nitrogen
  5. temperaturethe temperature of the reaction mass being maintained at about 70° C
  6. temperaturewas cooled to room temperature
  7. distillationto distillation

Sources & evidence

ORD record
ord-cbb47104230840fbb54142cd61d56e4c
Source dataset
uspto-grants-1985_12
Patent number
US04558111

Linked notes

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