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

HRID 375596Notes

Reaction equation

HRID 375596 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1.Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH:11][C:12]([OH:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 680093-Fluorobenzaldehyde

Product 1

HCID 886063-(3-Fluorophenyl)-2-propenoic acidYield 84.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-fluorobenzaldehyde (10 g), malonic acid (15.6 g) and piperidine (0.7 ml) in pyridine (35 ml) was heated at reflux for 3.5 hours. After cooling to room temperature, the reaction mixture was added to a mixture of ice water (210 ml) and conc. hydrochloric acid (56 ml). The precipitate was isolated by filtration and recrystallized from methanol/water to give 3-fluorocinnamic acid (11.3 g).

Workup

  1. temperatureat reflux for 3.5 hours
  2. customThe precipitate was isolated by filtration
  3. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-0ab4bc206d6443ffa8fdff5b852c4ac4
Source dataset
uspto-grants-1996_01
Patent number
US05486541

Reaction notes

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