Acetic Acid → 80540-68-7
Reaction equation
[C:1]1([CH3:9])[C:2](C=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:10]([CH2:12][C:13]([OH:15])=[O:14])#[N:11].[C:16](O)(=O)C.C([O-])(=O)C.[NH4+]>C(O)C>[C:10]([C:12](=[CH:9][C:1]1[CH:6]=[CH:5][C:4]([CH3:16])=[CH:3][CH:2]=1)[C:13]([OH:15])=[O:14])#[N:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Tolualdehyde (400 g), cyanoacetic acid (311 g), acetic acid (60 ml) and ammonium acetate (25.6 g) were refluxed for 4 hours by heating in ethyl alcohol (1.6 l). After the reaction, ethyl alcohol was concentrated to 600 ml under a reduced pressure, and it was poured in 1 liter of iced water to separate crystals. The separated crystals were filtered out by suction to obtain 2-cyano-3-(4-methylphenyl)acrylic acid which melted at 210°-215° C. in a yield of 560 g. This compound (320 g) and thionyl chloride (252 g) were dissolved in acetonitrile (200 ml) by heating for 1 hour. After the reaction, acetonitrile and thionyl chloride were distilled off under a reduced pressure, and the resulting solid was added to a solution composed of hydroxyethyl methacrylate (244.8 g), pyridine (149 g) and acetonitrile (2 liters). The reaction was carried out for 2 hours while keeping the reaction temperature at 40° C. or less. After the reaction, the reaction solution was poured in iced water to separate crystals. The resulting crystals were recrystallized from ethyl alcohol (3 liters) to obtain 360 g of the desired product which melted at 74°-75° C.
Workup
- concentrationwas concentrated to 600 ml under a reduced pressure, and it
- additionwas poured in 1 liter of iced water
- customto separate crystals
- filtrationThe separated crystals were filtered out by suction
Sources & evidence
- ORD record
- ord-a807c31528e34848917106456c526521
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04645735
Reaction notes
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