Diethyl Ether → 4-Chlorocinnamoyl chloride

HRID 1731215Notes

Reaction equation

HRID 1731215 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O.CCOCC>CN(C)C=O>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([Cl:15])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 153712-Propenoic acid, 3-(4-chlorophenyl)-HCID 24386Thionyl Chloride

Product 1

HCID 534112944-Chlorocinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 8.00 g. of p-chlorocinnamic acid and 4.72 ml. of thionyl chloride in 50 ml. ether is added 1.01 ml. of dimethyl formamide. Two liquid phases are then formed and the reaction mixture is stirred overnight at room temperature. The upper phase is decanted and the solvent evaporated from it to yield p-chlorocinnamoyl chloride.

Workup

  1. additionTo a mixture of 8.00 g
  2. customTwo liquid phases are then formed
  3. customThe upper phase is decanted
  4. customthe solvent evaporated from it

Sources & evidence

ORD record
ord-f9253a1315ba4073bf045ae38b2d08fb
Source dataset
uspto-grants-1976_11
Patent number
US03995054

Reaction notes

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