Hydrochloric Acid → HCID 20431656, compound
Reaction equation
[C:1]([C:3](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C-:17]#[N:18].[Na+].C(Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:1]([CH:3]([CH:9]([C:17]#[N:18])[C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]Participants
Procedure
A mixture of-ethyl 2-cyano-3-(4-hydroxyphenyl)-2-propenoate (150 g, 0.69 mole), sodium cyanide (35.8 g, 0.73 mole, 5.8 percent excess), chloroform (500 ml), water (450 ml) and benzyltriethylammonium chloride (3.5 g), is stirred under nitrogen at room temperature for 50 minutes. By this time, all the solid reagents are dissolved. Concentrated hydrochloric acid (115 ml) is added to the mixture and the chloroform layer removed. The residue is extracted with ethyl acetate. Each of the organic layers is washed with water and dried over anhydrous magnesium sulfate. Upon removal of the solvents, 22.4 g (13.4 percent) of ethyl 2,3-dicyano-3-(4-hydroxyphenyl)propionate is isolated from the chloroform layer, and 140 g (83 percent) of the same product is isolated from the ethyl acetate layer. The combined yield is 96.4 percent.
Workup
- dissolutionBy this time, all the solid reagents are dissolved
- customthe chloroform layer removed
- extractionThe residue is extracted with ethyl acetate
- washEach of the organic layers is washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customUpon removal of the solvents
Sources & evidence
- ORD record
- ord-dfae9f5cac4a4b57b170027cf7bec50d
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04493799
Reaction notes
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