Methacrylic Acid → Benzophenone

HRID 2210612Notes

Reaction equation

HRID 2210612 reaction equation
[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([OH:24])(=[O:23])[C:20]([CH3:22])=[CH2:21].O[C:26]1[CH:39]=[CH:38][C:29]([C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])=[CH:28][CH:27]=1>C(O)(C)C>[C:19]([O-:24])(=[O:23])[C:20]([CH3:22])=[CH2:21].[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:31])[C:29]1[CH:38]=[CH:39][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 4093Methacrylic AcidHCID 143474-HydroxybenzophenoneHCID 2723671Tetrabutylammonium Hydroxide

Product 2

HCID 3102BenzophenoneHCID 87595Methacrylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

In the following example, a terpolymer derivative having 0.88 mole % methacrylate and 0.07 mole % benzophenone (graft ratio 92.7%:7.3% methacrylate:benzophenone) was prepared by a procedure to Example A-3 except that the tetrabutylammonium salt was prepared by charging 101.3 mL tetrabutylammonium hydroxide (1.0 M in methanol), 8.3 g (8.2 mL) methacrylic acid, 1.01 g 4-hydroxybenzophenone, and 100 mL isopropanol to a second flask and stirring at room temperature to give a translucent yellowish solution. This mixture was then added to the polymeric cement, as in Example 4. The polymer was isolated by precipitation in isopropanol with 0.1% BHT stabilizer optionally added. 1HNMR (400 MHz, CDCl3) analysis confirmed 97.3% conversion of benzylic bromide to grafted species. These results are given in Table A.

Workup

  1. customwas prepared
  2. customto give a translucent yellowish solution
  3. additionThis mixture was then added to the polymeric cement, as in Example 4
  4. additionoptionally added

Sources & evidence

ORD record
ord-73f4fa953e8c490a85e2ecc50c7c54b2
Source dataset
uspto-grants-1995_10
Patent number
US05459174

Reaction notes

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