4-Methoxy cinnamic acid → 4-Methoxycinnamic acid chloride

HRID 2108222Notes

Reaction equation

HRID 2108222 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9](O)=[O:10])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([Cl:16])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 132454-Methoxy cinnamic acidHCID 24386Thionyl Chloride

Product 1

HCID 534017724-Methoxycinnamic acid chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 1000 mL round bottom flask equipped with a magnetic stir bar, reflux condenser, dropping funnel, and argon inlet is charged with 30.0 g (0.17 mol) of 4-methoxycinnamic acid and 500 ml of benzene. Next, 40.5 ml (66.1 g, 0.56 mol) of thionyl chloride is added dropwise. After the addition is complete, the reaction mixture is heated to reflux for five hours. Heating is discontinued and the mixture allowed to stir overnight. The benzene is removed by rotary evaporation to yield 33.6 g (0.17 mol, 100%) of a beige solid. Proton NMR and IR are consistent with the proposed structure. This material is used without further purification.

Workup

  1. customA 1000 mL round bottom flask equipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. additionAfter the addition
  4. temperaturethe reaction mixture is heated
  5. temperatureto reflux for five hours
  6. temperatureHeating
  7. customThe benzene is removed by rotary evaporation

Sources & evidence

ORD record
ord-0414b4a6dc614ae1809eb25730280541
Source dataset
uspto-grants-1990_06
Patent number
US04937370

Reaction notes

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