Water → Deca-8-yl acrylate

HRID 280903Notes

Reaction equation

HRID 280903 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[CH2:4].[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>C1(C)C=CC=CC=1>[C:2]([O:6][CH:12]([CH2:7][CH3:17])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:21][CH2:20][CH3:26])(=[O:5])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 6581Acrylic AcidHCID 90154-Methoxyphenol

Product 1

HCID 17853765Deca-8-yl acrylateYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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, 1588 g of acrylic acid, 2700 g of toluene, 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 87°-92° C. under 0.7 mmHg. The distillate was washed with an aqueous solution of 2% KOH, washed with water, dehydrated and filtered to give tricyclo[5.2.1.02,6 ]deca-8-yl acrylate (hereinafter referred to as "TCD-AA") in 70% 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 aqueous solution of 2% KOH
  9. washwashed with water
  10. filtrationfiltered

Sources & evidence

ORD record
ord-c0916c5240f640f5a41fb9d92ef1409b
Source dataset
uspto-grants-1986_05
Patent number
US04591626

Reaction notes

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