Malonic Acid → HCID 22256048, compound

HRID 1611750Notes

Reaction equation

HRID 1611750 reaction equation
O[C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5](C=O)=[CH:4][C:3]=1[O:12][CH3:13].C(O)(=O)CC(O)=[O:17].N1[CH2:26][CH2:25]CCC1>C(O)=O>[CH3:11][O:10][C:9]1[CH:8]=[C:5]([OH:17])[CH:4]=[C:3]([O:12][CH3:13])[C:2]=1[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 8655Syringaldehyde

Product 1

HCID 22256048HCID 22256048, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 4-hydroxy-3,5-dimethoxy benzaldehyde (2.5 g, 0.013 mol), malonic acid (2.80 g, 0.027 mol), piperidine (2–5 mL) and formic acid (10–20 mL) were taken in a 100 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well and placed inside the microwave oven and irradiated for 2–8 minutes in parts. The cooled mixture was poured into ice cold water and extracted with ethyl acetate. The organic layer was washed with dil HCl., saturated sodium chloride and then organic layer dried over sodium sulphate. The solvent was evaporated under reduced pressure to obtain liquid which was purified on silica gel column chromatography using mixture of hexane and ethyl acetate (9:1 to 6:4), provided a viscous liquid in 37% yield; 1H NMR (CDCl3) δ 6.73(1H, s, H-3 and H-5), 6.62 (1H, dd, CH═CH2) 5.61 (1H, d, J=18.6 Hz, cis-CH═CH2), 5.16(1H, d, J=10.8, trans-CH═CH2); 13C NMR (CDCl3) δ 147.4 (C-2) and C-6), 137.2 (C-1), 135.1 (CH═CH2), 129.5 (C-4), 112.2 (CH═CH2), 103.3 (C-3 and C-5), 56.0 (2-OMe).

Workup

  1. customfitted with a loose funnel at the top
  2. customirradiated for 2–8 minutes in parts
  3. additionThe cooled mixture was poured into ice cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with dil HCl
  6. dry with material, saturated sodium chloride and then organic layer dried over sodium sulphate
  7. customThe solvent was evaporated under reduced pressure
  8. customto obtain liquid which
  9. customwas purified on silica gel column chromatography
  10. additionmixture of hexane and ethyl acetate (9:1 to 6:4)
  11. customprovided a viscous liquid in 37% yield

Sources & evidence

ORD record
ord-894b88cae7864e969c9ba265cf483b65
Source dataset
uspto-grants-2006_01
Patent number
US06989467B2

Reaction notes

Loading…