Hydrochloric Acid → Phthalonitrile
Reaction equation
O[C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[C:3]=1[C:10]#[N:11].C(=O)([O-])[O-].[K+].[K+].ClC([Si](C)(C)C)C.Cl>CN(C)C=O>[C:10](#[N:11])[C:3]1[C:4](=[CH:7][CH:8]=[CH:9][CH:2]=1)[C:5]#[N:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In 200 ml of N,N-dimethylformamide were dissolved with heating 20 g of 3-hydroxyphthalonitrile and 10.55 g of potassium carbonate, to which 20 g of 1-chloroethyl-trimethylsilane were added dropwise at 30° C. in the atmosphere of argon. Immediately after the addition, the mixture was stirred for 36 hours while maintaining the reaction temperature at 85°-100° C. The reaction vessel was then cooled to room temperature and 200 ml of dilute hydrochloric acid was added. The mixture was extracted with 1 liter of toluene. The organic layer was washed well with water and water was removed with magnesium sulfate. Thereafter, toluene was removed by distillation and the residue was purified with a toluene/silica gel column to obtain 16.9 g (yield: 49.9%) of a compound having the formula (XVIII) below. The compound is in the form of white crystals and has a melting point of 67.5° C. The IR spectrum of the compound is shown in FIG. 4. ##STR40##
Workup
- additionImmediately after the addition
- temperaturewhile maintaining the reaction temperature at 85°-100° C
- extractionThe mixture was extracted with 1 liter of toluene
- washThe organic layer was washed well with water and water
- customwas removed with magnesium sulfate
- customThereafter, toluene was removed by distillation
- customthe residue was purified with a toluene/silica gel column
Sources & evidence
- ORD record
- ord-26200d04cbbf4b1495ed701ff2a2acb3
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677025
Reaction notes
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