Malonic Acid → (E)-3-(2,5-difluoro-4-methoxy-phenyl)-acrylic acid

HRID 404310

Reaction equation

HRID 404310 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([F:12])=[CH:6][C:3]=1[CH:4]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16]>CCO.N1C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([F:12])=[CH:6][C:3]=1/[CH:4]=[CH:14]/[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 38569382,5-Difluoro-4-methoxybenzaldehyde

Product 1

HCID 5928340(E)-3-(2,5-difluoro-4-methoxy-phenyl)-acrylic acidYield 74%

Reagents, catalysts & solvents 1

HCID 21975839Pyridine ethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 250 mL round bottom flask was charged with 2,5-difluoro-4-methyoxybenzaldehyde (commercially available from Manchester Organics Ltd., UK) (18.45 g, 107.2 mmol), malonic acid (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (12.27 g, 117.9 mmol), and 10:1 EtOH/pyridine (27 mL). The mixture was stirred overnight at 70° C. under a reflux condenser and cooled to 0° C. for 2 hours. The precipitated solid was filtered, rinsed with ether, and dried in vacuo to afford H3.1 (16.96 g, 74% yield) as a white powder.

Workup

  1. temperaturecooled to 0° C. for 2 hours
  2. filtrationThe precipitated solid was filtered
  3. washrinsed with ether
  4. customdried in vacuo
  5. customto afford H3.1 (16.96 g, 74% yield) as a white powder

Sources & evidence

ORD record
ord-060b17b6940d4708b390ae4dbd86790d
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Linked notes

Loading…