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

HRID 1382518Notes

Reaction equation

HRID 1382518 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].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[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

5

Reactant 3

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 90965Benzene, (1,3,3,3-tetrachloropropyl)-

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 129 g of 1,1,1,3-tetrachloro-3-phenylpropane, 74 g of glacial acetic acid, and 31 g of monohydrate of p-toluenesulphonic acid is heated while stirring to the boiling point 115° to 120° C. for 13 h with gradual addition of 18 g of water. The precipitated crystals are filtered off, washed with water, to give 59 g of cinnamic acid. Then, the filtrate, is condensed, crystals are filtered off and washed with water to give another 11 g of cinnamic acid with the total yield of 94.5% (melting point 131° to 133° C., min. 98% purity).

Workup

  1. temperatureis heated
  2. filtrationThe precipitated crystals are filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-086ec970d476449494c45ba10676da51
Source dataset
uspto-grants-1989_02
Patent number
US04806681

Reaction notes

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