4-Methoxyphenol → Dicyclopentadiene

HRID 1420154Notes

Reaction equation

HRID 1420154 reaction equation
[C:1](OCCC[Si](OC)(OC)OC)(=O)[C:2]([CH3:4])=[CH2:3].CO[C:19]1[CH:25]=[CH:24][C:22](O)=[CH:21][CH:20]=1>>[CH2:21]1[CH:1]2[CH:2]3[CH:4]=[CH:22][CH:24]([CH:25]2[CH:19]=[CH:20]1)[CH2:3]3

Participants

3

Reactant 2

HCID 90154-MethoxyphenolHCID 173183-(Trimethoxysilyl)propyl methacrylate

Product 1

HCID 6492DicyclopentadieneYield 70%

Conditions

Temperature
87.5 °C

Procedure

59.1 g (0.20 mol) 3-methacryloyloxypropyltrimethoxy silane and some hydroquinone monomethyl ether (MEHQ) are placed in a sulphonation flask which is connected via a distillation bridge to a cracking apparatus. After flushing with argon, cyclopentadiene is fed into the reaction vessel, with simultaneous stirring and warming to 85 to 90° C. After 33 hours the reaction has finished and formed dicyclopentadiene is distilled off at 0.05 mbar. Following subsequent fractional distillation in a high vacuum, the norbornene silane (1) (bp: 98°-100° C./7.0 mPa) is obtained as a colourless liquid in 70% yield.

Workup

  1. customAfter flushing with argon, cyclopentadiene

Sources & evidence

ORD record
ord-c2c4e067bd0043fca588f61407ada390
Source dataset
uspto-grants-1999_03
Patent number
US05889132

Reaction notes

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