Malonic Acid → 1081765-44-7

HRID 1852253Notes

Reaction equation

HRID 1852253 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C(O)(=O)[CH2:13][C:14]([OH:16])=[O:15]>N1C=CC=CC=1.N1CCCCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:13]/[C:14]([OH:16])=[O:15])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 867Malonic AcidHCID 27373584-Fluoro-3-methoxybenzaldehyde

Product 1

HCID 218898501081765-44-7Yield 97%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8082PiperidineSolvent

Procedure

To a solution of 4-fluoro-3-methoxybenzaldehyde (30 g, 195 mmol) in pyridine (134 ml) and piperidine (4.12 ml) was added malonic acid (30.4 g, 292 mmol) at room temperature. The reaction mass was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was acidified with 1.5N HCl solution. The precipitated solid was filtered washed with pet ether to get crude compound (37 g, 97%) as white solid. The crude compound was taken to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ ppm 12.37 (s, 1H), 7.59-7.55 (d, J=16 Hz, 1H), 7.53 (s, 1H), 7.26-7.22 (m, 2H), 6.59-6.55 (d, J=16 Hz, 1H), 3.89 (s, 3H); MS: MS m/z 195.0 (M+−1).

Workup

  1. temperatureThe reaction mass was refluxed for 18 h
  2. customThe solvent was evaporated under reduced pressure
  3. filtrationThe precipitated solid was filtered
  4. washwashed with pet ether

Sources & evidence

ORD record
ord-df16a25f6c544ae1851707eb1b311400
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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