Eugenol → 2-Methoxy-4-[3-(triethoxysilyl)propyl]phenol

HRID 1158560Notes

Reaction equation

HRID 1158560 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH:11]=[CH2:12])[CH:6]=[CH:7][C:8]=1[OH:9].[CH2:13]([O:15][SiH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[CH3:14]>[Pt].[H+].[H+].Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl.C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][CH2:12][Si:16]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])[O:15][CH2:13][CH3:14])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 2

HCID 3314EugenolHCID 13830Triethoxysilane

Product 1

HCID 231177322-Methoxy-4-[3-(triethoxysilyl)propyl]phenolYield 88%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 61859Chloroplatinic acidCatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

Into a four-neck flask provided with a stirrer, a reflux condenser, a dropping funnel and a thermometer were added 164 g (1.0 mole) of 3-(3-methoxy-4-hydroxyphenyl)propene and 100 ppm in terms of platinum metal of a 2 mass % isopropanol solution of chloroplatinic acid. Then 164 g (1.0 mole) of triethoxysilane was dripped over the course of five hours from a dropping funnel and was reacted while the mixture was heated and stirred at a temperature in the range from 50 to 60° C. After the reaction was completed, vacuum distillation was performed and 289 g (0.88 mole) of the desired product (3-(3-methoxy-4-hydroxyphenyl)propyl triethoxysilane) were obtained. The yield was 88%.

Workup

  1. customInto a four-neck flask provided with a stirrer, a reflux condenser, a dropping funnel
  2. customwas reacted while the mixture
  3. temperaturewas heated
  4. distillationvacuum distillation

Sources & evidence

ORD record
ord-9f499f745cc8436ea450a875e9a5fbae
Source dataset
uspto-grants-2010_10
Patent number
US07811637B2

Reaction notes

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