Acrylic Acid → Acryloxythexyldiisopropylsilane

HRID 2301009Notes

Reaction equation

[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C(N(CC)CC)C.[C:29]([Si:35]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])Cl)([CH:32]([CH3:34])[CH3:33])([CH3:31])[CH3:30]>C1(C)C=CC=CC=1>[C:1]([O:5][Si:35]([C:29]([CH:32]([CH3:34])[CH3:33])([CH3:31])[CH3:30])([CH:40]([CH3:41])[CH3:42])[CH:37]([CH3:38])[CH3:39])(=[O:4])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 80 °C

Procedure

A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 14.4 g (0.2 mol) of acrylic 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 38.6 g of a fraction having a boiling point of 87-92° 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 38.6 g of a fraction

Sources & evidence

ORD record: ord-37823d561bbf4f5f91e59e27c21aafc9
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498264B2

Reaction notes

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