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.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 180 ml of N,N-dimethylformamide were dissolved with heating 20 g of 3-hydroxyphthalonitrile and 10.55 g of potassium carbonate, to which 18 g of chloromethyltrimethyl-silane were added dropwise at 40° C. in the atmosphere of argon. After the addition, the mixture was stirred for 30 hours while maintaining the reaction temperature at 80°-90° C. The reaction vessel was then cooled to room temperature and 250 ml of dilute hydrochloric acid was added. The mixture was extracted with 1.2 liters 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 23.3 g (yield: 73.0%) of a compound having the formula (XII) below. The compound is in the form of white crystals and has a melting point of 112.5° C. The IR spectrum of the compound is shown in FIG. 3. ##STR37##
Workup
- additionAfter the addition
- temperaturewhile maintaining the reaction temperature at 80°-90° C
- extractionThe mixture was extracted with 1.2 liters 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-58d4871eba9a46168c4e5d179f46ce31
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677025
Reaction notes
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