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

HRID 1382519Notes

Reaction equation

HRID 1382519 reaction equation
ClC(Cl)(Cl)C[CH:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:14]([OH:17])(=[O:16])[CH3:15]>>[C:14]([OH:17])(=[O:16])[CH:15]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 90965Benzene, (1,3,3,3-tetrachloropropyl)-

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 76.3%

Procedure

A mixture of 129 g of 1,1,1,3-tetrachloro-3-phenylpropane, 74 g of glacial acetic acid and 39 g of Wolfatit OK 80 cation exchanger is heated to 118° to 124° C. for 15 h. The cation exchanger is removed from the hot reaction mixture by filtration. After cooling the mixture, filtration of the crystals and their washing with water, 56.5 g of cinnamic acid is obtained. Condensation of the filtrate followed by filtration of the crystals gives another 9.5 g of cinnamic acid with total yield of 89% (melting point after recrystallization 128° to 135° C., min. 98% purity).

Workup

  1. temperatureis heated to 118° to 124° C. for 15 h
  2. customThe cation exchanger is removed from the hot reaction mixture by filtration
  3. temperatureAfter cooling
  4. filtrationthe mixture, filtration of the crystals and their
  5. washwashing with water

Sources & evidence

ORD record
ord-375a1de0716446f4a4c6255759399667
Source dataset
uspto-grants-1989_02
Patent number
US04806681

Reaction notes

Loading…