Hydrochloric Acid → p-Cyanocinnamic acid

HRID 1439140Notes

Reaction equation

HRID 1439140 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].Cl>N1C=CC=CC=1.N1CCCCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:12][C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 660424-Cyanobenzaldehyde

Product 1

HCID 86773p-Cyanocinnamic acid

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
100 °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

  1. temperatureThe mixture was heated
  2. customAfter the reaction
  3. customThen, the resulting white precipitate was separated
  4. filtrationby filtering
  5. washwashed with dilute hydrochloric acid and water
  6. customwas recrystallized by use of glacial acetic acid

Sources & evidence

ORD record
ord-36ecb62a94a749aa945b12baa3b2cf1e
Source dataset
uspto-grants-1977_11
Patent number
US04058475

Reaction notes

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