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

HRID 1382523Notes

Reaction equation

HRID 1382523 reaction equation
ClC(Cl)(Cl)C[CH:4](Cl)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S(=O)(=O)(O)O.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[C:20]([OH:23])(=[O:22])[CH:21]=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 90965Benzene, (1,3,3,3-tetrachloropropyl)-

Product 1

HCID 87842-Propenoic acid, 3-phenyl-Yield 9.8%

Procedure

A mixture of 51.6 g of 1,1,1,3-tetrachloro-3-phenylpropane, 60 g of glacial acetic acid and 17.8 g of 55% sulphuric acid is refluxed under stirring at 115° to 122° C. for 5 h, after which time the evolution of hydrogen chloride ceases. The work-up of the reaction mixture as described in Example 1 yields 22.5 g and 2.9 g of cinnamic acid in 85.8% total yield (melting point 131.5° to 133° C., min. 99% purity).

Workup

  1. temperatureis refluxed

Sources & evidence

ORD record
ord-13167917bb734d70b8a04fb020b90512
Source dataset
uspto-grants-1989_02
Patent number
US04806681

Reaction notes

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