Thionyl Chloride → p-Acetoxy-cinnamic acid azide

HRID 259599Notes

Reaction equation

HRID 259599 reaction equation
[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](O)=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].S(Cl)(Cl)=O.[N-:20]=[N+:21]=[N-:22].[Na+]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([N:20]=[N+:21]=[N-:22])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 85857Cinnamic acid, p-hydroxy-, acetate

Product 1

HCID 54496664p-Acetoxy-cinnamic acid azide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

41.2 g (0.02 mol) of p-acetoxy-cinnamic acid are suspended in 100 ml of benzene and 29 ml (0.4 mol) of thionyl chloride are added. The reaction mixture is heated to the boil under a reflux condenser for half an hour and thereafter the solvent and excess thionyl chloride are removed by distillation in vacuo. The crude p-acetoxy-cinnamic acid chloride which remains is dissolved in 200 ml of absolute dimethoxyethane, 39 g (0.6 mol) of sodium azide are added and thereafter the mixture is stirred for 48 hours at room temperature. The inorganic salts are then filtered off and the filtrate is concentrated in vacuo at 30° C. Hereupon, colourless crystals separate out. The crystallisation is completed by adding ether. p-Acetoxy-cinnamic acid azide of melting point 114° C. (decomposition) is obtained.

Workup

  1. temperatureThe reaction mixture is heated to the boil under a reflux condenser for half an hour
  2. customthe solvent and excess thionyl chloride are removed by distillation in vacuo
  3. dissolutionThe crude p-acetoxy-cinnamic acid chloride which remains is dissolved in 200 ml of absolute dimethoxyethane
  4. filtrationThe inorganic salts are then filtered off
  5. concentrationthe filtrate is concentrated in vacuo at 30° C
  6. customHereupon, colourless crystals separate out
  7. customThe crystallisation
  8. additionby adding ether

Sources & evidence

ORD record
ord-2868c2fa0a764eaba00006438f227ed4
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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