Acetic Acid → Diethyl 2-(3,4-dimethoxybenzylidene)malonate

HRID 424605Notes

Reaction equation

HRID 424605 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.[CH2:13]([O:15][C:16](=[O:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:14].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[CH2:13]([O:15][C:16](=[O:23])[C:17](=[CH:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 8419Veratraldehyde

Product 1

HCID 335552Diethyl 2-(3,4-dimethoxybenzylidene)malonate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

3,4-dimethoxybenzaldehyde (Veratraldehyde) (9.13 g, 55 mM) was heated with malonic acid diethyl ester (8.00 g, 50 mM), acetic acid (0.29 ml) and piperidine (0.74 ml) in benzene (100 ml) in an apparatus equipped with a water separator (Dean-Stark tube) until 50 mM water was separated. After washing the benzene solution with water, it was dried over anhydrous magnesium sulfate. After drying, benzene was evaporated under reduced pressure to obtain a crude product (15.40 g). The crude product thus obtained is pure enough, and can be used in the subsequent reaction without further purification.

Workup

  1. customwas separated
  2. washAfter washing the benzene solution with water, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customAfter drying
  5. custombenzene was evaporated under reduced pressure
  6. customto obtain a crude product (15.40 g)

Sources & evidence

ORD record
ord-47ee0ab220f04305ba10fa44f3dc9857
Source dataset
uspto-grants-2012_01
Patent number
US08106053B2

Reaction notes

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