Thionyl Chloride → HCID 53880412, compound

HRID 597665Notes

Reaction equation

HRID 597665 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][C:17](=[O:19])[CH3:18])[CH:8]=[CH:9][C:10](O)=[O:11])[CH:2]=[CH2:3].S(Cl)(Cl)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>C1C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][C:17](=[O:19])[CH3:18])[CH:8]=[CH:9][C:10]([N:24]=[N+:25]=[N-:26])=[O:11])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 53788381HCID 53788381, compound

Product 1

HCID 53880412HCID 53880412, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

26.2 g (0.1 mol) of 3-allyloxy-4-acetoxy-cinnamic acid are suspended in 90 ml of benzene and 14.6 ml (0.2 mol) of thionyl chloride are added. The reaction mixture is heated to the boil under reflux for 30 minutes. Thereafter the solvent and the excess thionyl chloride are removed by distillation under reduced pressure. The crude 3-allyloxy-4-acetoxy-cinnamic acid chloride which is left is dissolved in 100 ml of absolute dimethoxyethane, 19.5 g (0.3 mol) of sodium azide are added and the reaction mixture is subsequently stirred for 48 hours at room temperature. The inorganic salts are then filtered off and the filtrate is concentrated under reduced pressure at 30° C. Hereupon, colourless crystals separate out. The crystallisation is completed by addition of ether. 3-Allyloxy-4-acetoxy-cinnamic acid azide of melting point 83°-84° C is obtained.

Workup

  1. temperatureThe reaction mixture is heated to the boil
  2. temperatureunder reflux for 30 minutes
  3. customThereafter the solvent and the excess thionyl chloride are removed by distillation under reduced pressure
  4. waitThe crude 3-allyloxy-4-acetoxy-cinnamic acid chloride which is left
  5. dissolutionis dissolved in 100 ml of absolute dimethoxyethane
  6. filtrationThe inorganic salts are then filtered off
  7. concentrationthe filtrate is concentrated under reduced pressure at 30° C
  8. customHereupon, colourless crystals separate out
  9. customThe crystallisation
  10. additionis completed by addition of ether

Sources & evidence

ORD record
ord-c4fd5dfda2a94a5a9e5dd2cad9abd4c9
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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