Malonic Acid → HCID 53931656, compound

HRID 373371Notes

Reaction equation

HRID 373371 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:4]=1[CH:5]=O.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1C=CC=CC=1.N1CCCCC1>O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:4]=1[CH:5]=[CH:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 136083472,5-Dimethoxy-3,6-dimethylbenzaldehyde

Product 1

HCID 53931656HCID 53931656, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,5-dimethoxy-3,6-dimethylbenzaldehyde (5.0 g), malonic acid (3.8 g), pyridine (6 ml) and piperidine (0.3 ml) was refluxed for 25 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water and saturated saline and dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and recrystallized from ethanol to obtain 2,5-dimethoxy-3,6-dimethylcinnamic acid (4.1 g) (Compound A-22). The physical properties and NMR spectrum data thereof are shown in Table 1.

Workup

  1. temperaturewas refluxed for 25 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N hydrochloric acid, water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-295eaf9fccb84a41b851d63ef8e5f572
Source dataset
uspto-grants-1992_11
Patent number
US05162571

Reaction notes

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