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+].ClCCC[Si](C)(C)C.Cl>CN(C)C(=O)C.CS(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
Procedure
In 150 ml of an N,N-dimethylacetamide/dimethylsulfoxide (=5/1 volume ratio) mixed solvent were dissolved 20 g of 3-hydroxyphthalonitrile and 10.55 g of potassium carbonate, to which 31.4 g of 3-chloropropyltrimethylsilane were added dropwise at 45° C. Immediately after the addition, the mixture was stirred for 24 hours while maintaining the reaction temperature at 90°-110° C. The reaction mixture was then cooled to room temperature and 180 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, followed by the removal of water with magnesium sulfate and the purification with a toluene/silica gel column, thereby to obtain 25.5 g (yield: 71.2%) of a compound having the following formula (XIX). The compound is in the form of white crystals and has a melting point of 145° C. The IR spectrum of the compound is shown in FIG. 5. ##STR41##
Workup
- additionImmediately after the addition
- temperaturewhile maintaining the reaction temperature at 90°-110° C
- extractionThe mixture was extracted with 1.2 liters of toluene
- washThe organic layer was washed well with water
- customfollowed by the removal of water with magnesium sulfate
- customthe purification with a toluene/silica gel column
Sources & evidence
- ORD record
- ord-d8705430274f43f68074a2688053d954
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05677025
Reaction notes
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