4-Methoxy cinnamic acid → 4-Methoxycinnamic acid chloride

HRID 2192765Notes

Reaction equation

HRID 2192765 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.O=S(Cl)[Cl:16]>>[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

3

Reactant 2

HCID 132454-Methoxy cinnamic acidHCID 24386Thionyl Chloride

Product 1

HCID 534017724-Methoxycinnamic acid chlorideYield 62%

Procedure

53.5 g of the 4-methoxy cinnamic acid (Aldrich 0.3 mol)) and 124.9 g of SOCl2 (Thionyl Chloride, 1.05 mol) were put into the two-neck flask having the volume of 250 ml, and then reacted with each other at normal temperature for 24 hours. After the reaction was finished, the distillation was performed to remove an excessive amount of SOCl2, and the reactant was diluted with 100 ml of toluene and neutralized by using the NaHCO3 solution. After the neutralization, the resulting substance was dried by using anhydrous MgSO4, and filtered, and the solvent was removed by using the rotary evaporator. Next, the substance was passed through the silica gel to remove the impurity, thus obtaining 36.5 g of the white solid (yield: 62%).

Workup

  1. customreacted with each other at normal temperature for 24 hours
  2. distillationthe distillation
  3. customto remove an excessive amount of SOCl2
  4. additionthe reactant was diluted with 100 ml of toluene
  5. customAfter the neutralization, the resulting substance was dried
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customthe rotary evaporator
  9. customto remove the impurity

Sources & evidence

ORD record
ord-3baa7f4abfbd458bbe140467955c93a9
Source dataset
uspto-grants-2012_12
Patent number
US08329841B2

Reaction notes

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