Thionyl Chloride → p-Cyanocinnamic acid chloride
Reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13](O)=[O:14])=[CH:9][CH:8]=1)#[N:6]>>[C:5]([C:7]1[CH:17]=[CH:16][C:10]([CH:11]=[CH:12][C:13]([Cl:3])=[O:14])=[CH:9][CH:8]=1)#[N:6]Participants
Conditions
- Temperature
- 80 °C
Procedure
0.2mol of p-cyanobenzaldehyde and 0.3mol of malonic acid were dissolved in 80ml of pyridine at room temperature, and 30 drops of piperidine were added thereto. The mixture was heated and stirred for 4 hours at about 100° C. After the reaction, the solution was poured slowly into dilute hydrochloric acid (250ml hydrochloric acid/250g water). Then, the resulting white precipitate was separated by filtering and washed with dilute hydrochloric acid and water, and was recrystallized by use of glacial acetic acid to obtain p-cyanocinnamic acid. 0.3mol of thionyl chloride was added to 0.1mol of the p-cyanocinnamic acid and the mixture was heated and stirred at about 80° C for 3 hours. An excess thionyl chloride was then removed under reduced pressure to obtain p-cyanocinnamic acid chloride.
Workup
- temperaturethe mixture was heated
- customAn excess thionyl chloride was then removed under reduced pressure
Sources & evidence
- ORD record
- ord-6fb080a787654cc29bbdfe03dedec883
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04058475
Reaction notes
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