Hydrochloric Acid → 3-(4-Fluorophenyl)-2-propenoic acid

HRID 1368009Notes

Reaction equation

HRID 1368009 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1.Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:11][C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 980703-(4-Fluorophenyl)-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.1 mol 4-fluorobenzaldehyde, 0.15 mol malonic acid, and 0.1 ml piperidine in 30 ml pyridine is boiled for 10 hours, cooled, and treated with 150 ml HCl having a 10% concentration. The precipitate is filtered and crystallized with ethanol. The yield of 4-fluorocinnamic acid is 68% and the melting point is 211° C.

Workup

  1. temperaturecooled
  2. concentrationa 10% concentration
  3. filtrationThe precipitate is filtered
  4. customcrystallized with ethanol

Sources & evidence

ORD record
ord-b589941efb524ab9970b66acb51292bd
Source dataset
uspto-grants-2003_06
Patent number
US06572939B2

Reaction notes

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