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

HRID 1382524Notes

Reaction equation

HRID 1382524 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]>S(=O)(=O)(O)O.O>[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

7

Reactant 4

HCID 176Acetic Acid2×HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 90965Benzene, (1,3,3,3-tetrachloropropyl)-

Product 1

HCID 87842-Propenoic acid, 3-phenyl-

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

A mixture of 77.4 g of 1,1,1,3-tetrachloro-3-phenylpropane, 7.7 g of 98% acetic acid and 1.8 g of 98% sulphuric acid is stirred and refluxed at 130° to 138° C. while a mixture of 15.5 g of water, 4 ml of acetic acid and 0.5 ml of sulphuric acid is gradually added over the period of 2.5 h, after which time the hydrogen chloride evolution ceases. The work-up of the reaction mixture as described in Example 1 gives 33.6 g of cinnamic acid in 75.6% total yield (melting point 132° to 133° C., min. 99% purity).

Workup

  1. additionis gradually added over the period of 2.5 h

Sources & evidence

ORD record
ord-ef892ecaf00b4ad2bca01385e04c6458
Source dataset
uspto-grants-1989_02
Patent number
US04806681

Reaction notes

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