Methacrylic Acid → Methacryloxy-tert-butyldiisopropylsilane

HRID 2301011Notes

Reaction equation

[C:1]([Si:5]([CH:10]([CH3:12])[CH3:11])([CH:7]([CH3:9])[CH3:8])Cl)([CH3:4])([CH3:3])[CH3:2].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.C(N(CC)CC)C.[C:36]([OH:41])(=[O:40])[C:37]([CH3:39])=[CH2:38]>C1(C)C=CC=CC=1>[C:36]([O:41][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])(=[O:40])[C:37]([CH3:39])=[CH2:38]

Participants

Conditions

Temperature: 80 °C

Procedure

A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 41.4 g (0.20 mol) of tert-butyldiisopropylchlorosilane, 60 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, 18.9 g (0.22 mol) of methacrylic acid was added dropwise over one hour. After the completion of dropwise addition, the reaction solution was stirred for 2 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 45.4 g of a fraction having a boiling point of 93-95° C./0.27 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 45.4 g of a fraction

Sources & evidence

ORD record: ord-da9b693ca5994d2492c23dba84f96fe8
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498264B2

Reaction notes

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