Guaiacol → Tri-isopropyl silyl acrylate

HRID 1981559Notes

Reaction equation

HRID 1981559 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].C(N(CC)CC)C.COC1C=CC=CC=1O.[CH:22]([Si:25]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])Cl)([CH3:24])[CH3:23]>C1(C)C(C)=CC=CC=1>[C:1]([O:5][Si:25]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:22]([CH3:24])[CH3:23])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 6581Acrylic AcidHCID 8471TriethylamineHCID 139400Triisopropylsilyl chloride

Product 1

HCID 167468Tri-isopropyl silyl acrylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

72.1 g (1 mol) of glacial acrylic acid, 101.2 g (1 mol) of triethylamine 0.072 g of methoxyphenol and 300 ml of xylene is added to a four-neck, round bottom flask equipped with a stirrer, condenser, nitrogen inlet, thermometer and dropping funnel. Under a nitrogen blanket, a solution of 192.8 g (1 mol) of triisopropylchlorosilane in 100 ml of xylene is slowly added to the rapidly stirred reactants at room temperature. The temperature is permitted to rise to a maximum temperature of 55° C. and this temperature is maintained with cooling if necessary.

Workup

  1. customequipped with a stirrer, condenser, nitrogen inlet
  2. customto rise to a maximum temperature of 55° C.
  3. temperaturethis temperature is maintained
  4. temperaturewith cooling if necessary

Sources & evidence

ORD record
ord-791b961d8a4c42dd928ad0b09256e68d
Source dataset
uspto-grants-1986_06
Patent number
US04593055

Reaction notes

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