Methacrylic Acid → Deca-8-yl methacrylate

HRID 280902Notes

Reaction equation

HRID 280902 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.CO[C:20]1[CH:26]=CC(O)=C[CH:21]=1>O>[C:1]([O:6][CH:12]([CH2:7][CH3:17])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:21][CH2:20][CH3:26])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 4093Methacrylic AcidHCID 6101p-Toluenesulfonic acidHCID 90154-Methoxyphenol

Product 1

HCID 22140531Deca-8-yl methacrylateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 10-liter separable flask equipped with a stirrer, a condenser and a water separator, 2700 g of tricyclo [5.2.1.02,6 ]deca-8-ol (white crystal powder), 1896 g of methacrylic acid, 2700 g of toluence, 135 g of p-toluenesulfonic acid and 0.64 g of hydroquinone monomethyl ether were placed and reacted at 115° C. with stirring for 2 hours while removing the water generated out of the system. Then, the reaction solution was taken out of the flask and then subjected to distillation to remove low boiling point components. Then, 15 g of hydroquinone monomethyl ether was added to the resulting solution and distillation under reduced pressure was conducted to isolate a distillate having a boiling point of 90°-95° C. under 0.7 mmHg. The distillate was washed with an agueous solution of 2% KOH, washed with water, dehydrated and filtered to give tricyclo[5.2.1.02,6 ]deca-8-yl methacrylate (hereinafter referred to as "TCD-MA") in 80% yield and 99.5 % purity.

Workup

  1. customIn a 10-liter separable flask equipped with a stirrer, a condenser
  2. customreacted at 115° C.
  3. customwhile removing the water
  4. distillationsubjected to distillation
  5. customto remove low boiling point components
  6. additionThen, 15 g of hydroquinone monomethyl ether was added to the resulting solution and distillation under reduced pressure
  7. customto isolate a distillate
  8. washThe distillate was washed with an agueous solution of 2% KOH
  9. washwashed with water
  10. filtrationfiltered

Sources & evidence

ORD record
ord-6788eb50112040a99233e8cd6a34197b
Source dataset
uspto-grants-1986_05
Patent number
US04591626

Reaction notes

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