Malonic Acid → 3-(4-Fluoro-2-methylphenyl)-2-propenoic acid

HRID 2047456Notes

Reaction equation

HRID 2047456 reaction equation
N1C=CC=CC=1.N1CCCCC1.[C:13](O)(=O)[CH2:14][C:15]([OH:17])=[O:16].[F:20][C:21]1[CH:28]=[CH:27][C:24](C=O)=[C:23]([CH3:29])[CH:22]=1>O>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[C:23]([CH3:29])[CH:22]=1

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 27832174-Fluoro-2-methylbenzaldehyde

Product 1

HCID 573678683-(4-Fluoro-2-methylphenyl)-2-propenoic acidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of pyridine (0.035 mL) and piperidine (1.43 mL) was added malonic acid (30 g), and the mixture was heated to 75° C. To this mixture was added dropwise 4-fluoro-2-methylbenzaldehyde (20 g), and the mixture was stirred at 90° C. for 6 hr. The reaction mixture was cooled to room temperature, and diluted with water (100 ml), and concentrated under reduced pressure. The residue was suspended in 0.1N hydrochloric acid (250 mL), and the mixture was stirred at room temperature for 30 min. The precipitate was collected by filtration, washed with 0.1N hydrochloric acid (250 mL) and water (50 mL, 0.3 times) and dried to give 4-fluoro-2-methylcinnamic acid (24 g, 93%) as a white powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with 0.1N hydrochloric acid (250 mL) and water (50 mL, 0.3 times)
  6. customdried

Sources & evidence

ORD record
ord-b60fbc897e1d4d799095ad510026c7a9
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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