Malonic Acid → HCID 58604057, compound

HRID 2113668Notes

Reaction equation

HRID 2113668 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([F:12])[CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:14]/[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 58604077HCID 58604077, compound

Product 1

HCID 58604057HCID 58604057, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 2-Chloro-4-fluoro-3-methoxybenzaldehyde (17.6 g, 93.3 mmol) and malonic acid (18.6 g, 179 mmol) was added pyridine (60 mL) followed by piperidine (1.6 mL, 19 mmol). The mixture was heated in a 90° C. oil bath giving a clear yellow solution. After 220 minutes, the hot solution was poured into 500 mL of ice cold 2.5N HCl with stirring. The resulting solid was isolated by filtration, washing thoroughly with water. Drying under vacuum gave (2E)-3-(2-chloro-4-fluoro-3-methoxyphenyl)acrylic acid as a yellow solid.

Workup

  1. customgiving a clear yellow solution
  2. customThe resulting solid was isolated by filtration
  3. washwashing thoroughly with water
  4. customDrying under vacuum

Sources & evidence

ORD record
ord-95ad2bbdfc9e471db089e1ef96e70410
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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