2-Propenoic acid, 3-(4-chlorophenyl)- → 4-Chlorocinnamoyl chloride

HRID 856970Notes

Reaction equation

HRID 856970 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12](O)=[O:13])=[CH:8][CH:7]=1>ClCCl>[Cl:5][C:6]1[CH:16]=[CH:15][C:9]([CH:10]=[CH:11][C:12]([Cl:3])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 534112944-Chlorocinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
43 °C

Procedure

7 ml of thionyl chloride are added dropwise to a suspension of 1.75 g of 4-chlorocinnamic acid in 40 ml of anhydrous dichloromethane, with stirring at 43° C. After reacting for 3 hours, the excess acid that has not reacted remains undissolved and is removed by decanting. The filtrate is evaporated to dryness, yielding 4-chlorocinnamic acid chloride.

Workup

  1. customthe excess acid that has not reacted
  2. customis removed
  3. customby decanting
  4. customThe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-f52c6b4a6ae742ceb3acef6daa07b43c
Source dataset
uspto-grants-2006_12
Patent number
US07144891B2

Reaction notes

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