Methacrylic Acid → Methacryloxythexyldiisopropylsilane

HRID 2301008Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C(N(CC)CC)C.[C:30]([Si:36]([CH:41]([CH3:43])[CH3:42])([CH:38]([CH3:40])[CH3:39])Cl)([CH:33]([CH3:35])[CH3:34])([CH3:32])[CH3:31]>C1(C)C=CC=CC=1>[C:1]([O:6][Si:36]([C:30]([CH:33]([CH3:35])[CH3:34])([CH3:32])[CH3:31])([CH:41]([CH3:42])[CH3:43])[CH:38]([CH3:39])[CH3:40])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 17.2 g (0.2 mol) of methacrylic acid, 120 ml of toluene, and 0.06 g of 2,6-di-tert-butyl-4-methylphenol. At room temperature, 22.3 g (0.22 mol) of triethylamine was added dropwise over one hour. At the end of dropwise addition, the flask was heated at 80° C. After the internal temperature became constant, 47.0 g (0.20 mol) of thexyldiisopropylchlorosilane was added dropwise over two hours. After the completion of dropwise addition, the reaction solution was stirred for 5 hours at 80° C. The reaction solution was then cooled to room temperature, and the resulting hydrochloric acid salt removed by filtration. The filtrate was distilled, collecting 43.2 g of a fraction having a boiling point of 92-97° C./0.13 kPa.

Workup

customA flask equipped with a stirrer
temperaturereflux condenser
additionAt the end of dropwise addition
additionAfter the completion of dropwise addition
temperatureThe reaction solution was then cooled to room temperature
customthe resulting hydrochloric acid salt removed by filtration
distillationThe filtrate was distilled
customcollecting 43.2 g of a fraction

Sources & evidence

ORD record: ord-a6ce985694a246aa91e6318bba65f23d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498264B2

Reaction notes

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