(2-Methoxy-4-prop-2-enylphenyl) acetate → Phenol, 2-methoxy-4-[3-(trimethoxysilyl)propyl]-, 1-acetate

HRID 411875Notes

Reaction equation

HRID 411875 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[CH2:13])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].[CH3:16][O:17][SiH:18]([O:21][CH3:22])[O:19][CH3:20]>[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][Si:18]([O:21][CH3:22])([O:19][CH3:20])[O:17][CH3:16])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7136(2-Methoxy-4-prop-2-enylphenyl) acetateHCID 17215Trimethoxysilane2×

Product 1

HCID 11232719Phenol, 2-methoxy-4-[3-(trimethoxysilyl)propyl]-, 1-acetate

Reagents, catalysts & solvents 1

HCID 61859Chloroplatinic acidCatalyst

Procedure

In the same reactor vessel, the 3-(4-acetoxy-3-methoxyphenyl)propene was heated to 80° C. and then charged with chloroplatinic acid (0.79 grams). Trimethoxysilane (1990 grams, 16.3 moles) was added with stirring to the reaction mixture over a period of 40 minutes. An ice bath was used to maintain the reaction mixture at a temperature of between 100 and 108° C. After the addition of the trimethoxysilane, the reaction mixture was held at 90° C. for 1 hour and then the mixture was cooled to room temperature. The product was distilled under vacuum at 143° C. and 1 mm Hg.

Workup

  1. customAn ice bath was used
  2. temperatureto maintain the reaction mixture at a temperature of between 100 and 108° C
  3. waitthe reaction mixture was held at 90° C. for 1 hour
  4. distillationThe product was distilled under vacuum at 143° C.

Sources & evidence

ORD record
ord-17cc0fbdf9664822bcf6dda098570bf0
Source dataset
uspto-grants-2003_05
Patent number
US06559329B2

Reaction notes

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