Malonic Acid → HCID 70116357, compound

HRID 1067406Notes

Reaction equation

HRID 1067406 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:4]=1[CH:5]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCC1>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:4]=1/[CH:5]=[CH:14]/[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 867Malonic AcidHCID 31268PyrrolidineHCID 47704302-methoxy-3,5-dimethylbenzaldehyde

Product 1

HCID 70116357HCID 70116357, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of 2-methoxy-3,5-dimethylbenzaldehyde (9.40 g, 57.2 mmol), malonic acid (8.90 g, 85.8 mmol), and pyrrolidine (730 mg, 8.58 mmol) in pyridine (80 mL) was refluxed for 14 hours. This reaction mixture was poured in iced water and extracted with ethyl acetate. The extract was washed with 2N-hydrochloric acid, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide 9.60 g of the title compound. Yield 81%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 2N-hydrochloric acid
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d8ad7d06bafa4a24b4e713c40cf216cb
Source dataset
uspto-grants-2001_06
Patent number
US06248766B1

Reaction notes

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