Hydrochloric Acid → 2-Propenoic acid, 3-(2-chloro-4-fluorophenyl)-

HRID 726143

Reaction equation

HRID 726143 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.Cl>N1C=CC=CC=1.O>[Cl:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[CH:12][C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 1450242-Chloro-4-fluorobenzaldehyde

Product 1

HCID 27250652-Propenoic acid, 3-(2-chloro-4-fluorophenyl)-Yield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a mixture of 2-chloro-4-fluorobenzaldehyde (20.0 g, 0.13 mol, Aldrich) and malonic acid (26.2 g, 0.25 mol, Aldrich) in pyridine (100 ml) at 50° C. was added dropwise piperidine (10 ml). After 18 h at 70° C., the mixture was poured into an ice cold solution of concentrated HCl (120 ml) and water (1.5 L). The resulting solid was filtered and washed repeatedly with water to give 24.4 g (96%) of 2-chloro-4-fluoro-cinnamic acid as a white solid: Recrystallization of 1.5 g from acetone:water mixtures gave 1.1 g of 2-chloro-4-fluorocinnamic acid as a white solid: mp 243°-245° C.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed repeatedly with water

Sources & evidence

ORD record
ord-7b250f591ac24bd79e4f5435df536049
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Linked notes

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