Malonic Acid → 3',4'-Dimethoxycinnamic acid

HRID 470597Notes

Reaction equation

HRID 470597 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.[OH-].[Na+]>N1C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:14][C:15]([OH:17])=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 867Malonic AcidHCID 8082PiperidineHCID 8419VeratraldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 168483',4'-Dimethoxycinnamic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Dimethoxybenzaldehyde (25 g, 0.15 mol), malonic acid (32.87 g, 0.31 mol) and piperidine (1 mL) were dissolved in pyridine (100 mL) under stirring. The reaction mixture was heated at 80° C. for 3 h, after which the temperature was further increased to 120° C. and maintained at this temperature for 3 h. The reaction mixture was cooled, diluted with water (70 mL) and pH of the solution was adjusted to 9 by addition of 10% aqueous sodium hydroxide solution. The mixture was extracted with ethyl acetate (3×150 mL). The pH of the aqueous layer was adjusted to 2 by addition of aqueous HCl (1:1) and the resulting solid was filtered and dried to afford the title compound.

Workup

  1. temperatureafter which the temperature was further increased to 120° C.
  2. temperaturemaintained at this temperature for 3 h
  3. temperatureThe reaction mixture was cooled
  4. extractionThe mixture was extracted with ethyl acetate (3×150 mL)
  5. additionThe pH of the aqueous layer was adjusted to 2 by addition of aqueous HCl (1:1)
  6. filtrationthe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-4772a03c378f49c48f80fbd7da6f7afb
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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