Acetic Acid → 2-Propenoic acid, 3-phenyl-

HRID 617004Notes

Reaction equation

HRID 617004 reaction equation
C1(N(C2C=CC=CC=2)[C:8]([CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])C=CC=CC=1.C(O)(=[O:26])C.S(=O)(=O)(O)O>O>[CH:10]([C:8]([OH:9])=[O:26])=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 2769635N,N-Diphenylcinnamamide

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The N,N-diphenylstyrenyl carboxamide-2% divinylbenzene copolymer from example 7(a) (53.0g) was heated with stirring at 130°-135° for 44 hours with a mixture of glacial acetic acid (670 ml.), concentrated sulphuric acid (500 ml.) and water (300 ml.). After cooling to room temperature, the mixture was filtered and the polymer washed successively with water (4 × 400 ml.), acetone (3 × 200 ml.); methanol (3 × 200ml.), water (2 × 400 ml.) and acetone (2 × 200 ml.); and dried in vacuo at 40° to constant weight. The title polymer (36.58g) was green in colour and exhibited ν max (NuJol) 1690 (C=O) and 3700-2400 (OH) cm-1. Titration was effected by suspending the product (0.500g) in 95% ethanol (50 ml.) adding 0.5M sodium hydroxide (50 ml.), warming the mixture to reflux, cooling and back titrating with 0.5M hydrochloric acid using phenolphthalein as the indicator; it was found that 47.12 ml. of acid were required for neutralisation indicating 2.88 m.mole carboxyl/g of polymer.

Workup

  1. filtrationthe mixture was filtered
  2. washthe polymer washed successively with water (4 × 400 ml.), acetone (3 × 200 ml.)
  3. customand dried in vacuo at 40° to constant weight
  4. additionadding 0.5M sodium hydroxide (50 ml.)
  5. temperaturewarming the mixture
  6. temperatureto reflux
  7. temperaturecooling

Sources & evidence

ORD record
ord-24fb597460b64e418f2601c5614a6296
Source dataset
uspto-grants-1978_02
Patent number
US04076913

Reaction notes

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