Benzene → HCID 86741824, compound

HRID 255394Notes

Reaction equation

HRID 255394 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[CH2:6]1[O:20][C:19]2[CH:18]=[CH:17][C:10]([CH2:11][C:12](=[CH2:16])[C:13]([O-:15])=[O:14])=[CH:9][C:8]=2[O:7]1.CC(N=NC(C#N)(C)C)(C#N)C.C1C=CC=CC=1>O1CCOCC1>[CH2:6]1[O:20][C:19]2[CH:18]=[CH:17][C:10]([CH2:11][C:12](=[CH2:16])[C:13]([O-:15])=[O:14])=[CH:9][C:8]=2[O:7]1.[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6547AzobisisobutyronitrileHCID 6581Acrylic AcidHCID 20165681HCID 20165681, compound

Product 1

HCID 86741824HCID 86741824, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A homogeneous mixture of 4 ml of peroxide-free dioxane, 5.124 g of acrylic acid, 1.639 g of 3,4-methylenedioxybenzylacrylate and 69 mg of AIBN is introduced into a vial previously dried in nitrogen atmosphere and bearing a tail-shape end, then the vial is flame-sealed and heated to 60° C. in a thermostat with stirring for 90 minutes. The vial contents are poured into benzene and the solid which is precipitated is filtered, dissolved in a little amount of dioxane and precipitated again in benzene. After further filtering and drying in the oven under vacuum at 30° C. overnight 5.193 g is obtained of the copolymer which is then subjected to fractionation by preparation of a 1% solution by weight of the same in dioxane and adding at a slow rate benzene dropwise to said solution while stirring and keeping the same at a constant temperature of 25° C. Three fractions are collected by filtration corresponding to a small amount of the top fraction, a useful center fraction and a large amount of a tail fraction. The center fraction of 2.86 g has an intrinsic viscosity in dioxane at 25° C. of 82.1 ml/g and an average molecular weight by osmometry of 35,000 dalton.

Workup

  1. additionis introduced into a vial
  2. custompreviously dried in nitrogen atmosphere
  3. customthe vial is flame-sealed
  4. additionThe vial contents are poured into benzene
  5. customthe solid which is precipitated
  6. filtrationis filtered
  7. dissolutiondissolved in a little amount of dioxane
  8. customprecipitated again in benzene
  9. filtrationAfter further filtering
  10. customdrying in the oven under vacuum at 30° C. overnight 5.193 g
  11. customis obtained of the copolymer which
  12. stirringwhile stirring
  13. customsame at a constant temperature of 25° C
  14. filtrationThree fractions are collected by filtration corresponding to a small amount of the top fraction
  15. customat 25° C.

Sources & evidence

ORD record
ord-e3d07bfce7474396a58856dc4d8f87de
Source dataset
uspto-grants-1987_10
Patent number
US04698171

Reaction notes

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