Thionyl Chloride → 3,4,5-Trihydroxybenzonitrile
Reaction equation
[C:1]([NH2:12])(=O)[C:2]1[CH:10]=[C:8]([OH:9])[C:6]([OH:7])=[C:4]([OH:5])[CH:3]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[C:1](#[N:12])[C:2]1[CH:3]=[C:4]([OH:5])[C:6]([OH:7])=[C:8]([OH:9])[CH:10]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A reaction mixture containing 23.5 g. of gallamide, 180 ml. of ethyl acetate and 35 ml. of thionylchloride was refluxed for about 18 hours. The volatile contents were removed by evaporation in vacuo and the resulting residue dissolved in 215 ml. of water. This aqueous solution was heated to about 90° C. until the evolution of gas had ceased. The aqueous solution was filtered through charcoal and the water removed from the filtrate by evaporation. 18 g. of gallonitrile were obtained melting at about 219° C. with decomposition (86% yield). Other nitriles useful as starting materials can be prepared similarly.
Workup
- additionA reaction mixture containing 23.5 g
- customThe volatile contents were removed by evaporation in vacuo
- dissolutionthe resulting residue dissolved in 215 ml
- filtrationThe aqueous solution was filtered through charcoal
- customthe water removed from the filtrate by evaporation
Sources & evidence
- ORD record
- ord-5b5f25eafe7642dd8bc0aa312c13b930
- Source dataset
- uspto-grants-1990_07
- Patent number
- US04942253
Reaction notes
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