Thionyl Chloride → 3-Allyl-4-acetoxy-cinnamic acid azide

HRID 597651Notes

Reaction equation

HRID 597651 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[CH:7]=[CH:8][C:9](O)=[O:10])[CH:2]=[CH2:3].S(Cl)(Cl)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>C1C=CC=CC=1>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[O:15][C:16](=[O:18])[CH3:17])[CH:7]=[CH:8][C:9]([N:23]=[N+:24]=[N-:25])=[O:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 538871623-Allyl-4-acetoxy-cinnamic acid

Product 1

HCID 540870003-Allyl-4-acetoxy-cinnamic acid azide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

22.2 g (0.09 mol) of 3-allyl-4-acetoxy-cinnamic acid are suspended in 100 ml of benzene and 13.2 ml (0.18 mol) of thionyl chloride are added. The reaction mixture is heated to the boil for half an hour under a reflux condenser and thereafter the solvent and excess thionyl chloride are removed by distillation under reduced pressure. The residual crude 3-allyl-4-acetoxy-cinnamic acid chloride is dissolved in 100 ml of absolute 1,2-dimethoxyethane, 17.5 g (0.27 mol) of sodium azide are added and the 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 adding ether. 3-Allyl-4-acetoxy-cinnamic acid azide of melting point 87°-89°C (decomposition) is obtained.

Workup

  1. temperatureThe reaction mixture is heated to the boil for half an hour under a reflux condenser
  2. customthe solvent and excess thionyl chloride are removed by distillation under reduced pressure
  3. dissolutionThe residual crude 3-allyl-4-acetoxy-cinnamic acid chloride is dissolved in 100 ml of absolute 1,2-dimethoxyethane
  4. filtrationThe inorganic salts are then filtered off
  5. concentrationthe filtrate is concentrated under reduced pressure at 30°C
  6. customHereupon, colourless crystals separate out
  7. customThe crystallisation
  8. additionby adding ether

Sources & evidence

ORD record
ord-b919a5cf41164c9c8c9f36e206ef6c65
Source dataset
uspto-grants-1977_03
Patent number
US04014920

Reaction notes

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