Malonic Acid → 2H-1-Benzopyran-3-carboxylic acid, 6-methyl-2-oxo-

HRID 276971Notes

Reaction equation

HRID 276971 reaction equation
[CH3:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11](O)(=[O:16])[CH2:12][C:13]([OH:15])=[O:14].N1C=CC=CC=1.NC1C=CC=CC=1>C(O)C.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:11](=[O:16])[C:12]([C:13]([OH:15])=[O:14])=[CH:7][C:6]=2[CH:9]=1

Participants

7

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 6115AnilineHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-

Product 1

HCID 250902H-1-Benzopyran-3-carboxylic acid, 6-methyl-2-oxo-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

2 g of 5-methylsalicylaldehyde (14.7 mmol), 3.06 g of malonic acid (29.4 mmol), 1.3 g of pyridine and 0.08 g of aniline are dissolved in a minimum amount of ethanol. The mixture is heated at 40° C. on a water bath for 6 h. Next, it is diluted with water, acidified and then extracted with ether. The solvent is removed by distillation under reduced pressure. The residue obtained is recrystallized from ethanol.

Workup

  1. extractionextracted with ether
  2. customThe solvent is removed by distillation under reduced pressure
  3. customThe residue obtained
  4. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-f1dfcf20fe7d423885f3648f9289de6e
Source dataset
uspto-grants-2002_03
Patent number
US06355658B1

Reaction notes

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