Methacrylic Acid → HCID 12040555, compound

HRID 2301010Notes

Reaction equation

HRID 2301010 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]([CH2:42][CH:43]([CH3:45])[CH3:44])([CH2:38][CH:39]([CH3:41])[CH3:40])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])([CH3:31])[CH3:32])([CH2:38][CH:39]([CH3:40])[CH3:41])[CH2:42][CH:43]([CH3:45])[CH3:44])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 4

HCID 4093Methacrylic AcidHCID 8471TriethylamineHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 9943182HCID 9943182, compound

Product 1

HCID 12040555HCID 12040555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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, 52.6 g (0.20 mol) of thexyldiisobutylchlorosilane 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 46.3 g of a fraction having a boiling point of 104-110° C./0.13 kPa.

Workup

  1. customA flask equipped with a stirrer
  2. temperaturereflux condenser
  3. additionAt the end of dropwise addition
  4. additionAfter the completion of dropwise addition
  5. temperatureThe reaction solution was then cooled to room temperature
  6. customthe resulting hydrochloric acid salt removed by filtration
  7. distillationThe filtrate was distilled
  8. customcollecting 46.3 g of a fraction

Sources & evidence

ORD record
ord-19f5ef2576dc4c4c8d65d90a0c9d47b3
Source dataset
uspto-grants-2002_12
Patent number
US06498264B2

Reaction notes

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