Thionyl Chloride → 4-Acetoxy-3-methoxy-cinnamic acid azide

HRID 259614

Reaction equation

HRID 259614 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][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[N-:22]=[N+:23]=[N-:24].[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:22]=[N+:23]=[N-:24])=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 757754-Acetoxy-3-methoxy-cinnamic acid

Product 1

HCID 539505664-Acetoxy-3-methoxy-cinnamic acid azide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

34.0 g (0.145 mol) of 4-acetoxy-3-methoxy-cinnamic acid are suspended in 150 ml of benzene and 21 ml (0.290 ml) of thionyl chloride are added. The mixture is then heated to the boil, under a reflux condenser, for 30 minutes; thereafter, the solvent and excess thionyl chloride are removed by distillation under reduced pressure. The crude 4-acetoxy-3-methoxycinnamic acid chloride which remains is dissolved in 150 ml of absolute 1,2-dimethoxyethane, 28.3 g (0.435 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., in the course of which colourless crystals separate out. The crystallisation is completed by adding ether. 4-Acetoxy-3-methoxy-cinnamic acid azide of melting point 93°-95° C. (decomposition) is obtained.

Workup

  1. temperatureThe mixture is then heated to the boil, under a reflux condenser, for 30 minutes
  2. customthereafter, the solvent and excess thionyl chloride are removed by distillation under reduced pressure
  3. dissolutionThe crude 4-acetoxy-3-methoxycinnamic acid chloride which remains is dissolved in 150 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., in the course of which colourless crystals
  6. customseparate out
  7. customThe crystallisation
  8. additionby adding ether

Sources & evidence

ORD record
ord-e6a5e20df68b4980a3a2cfb4d075218c
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Linked notes

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