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

HRID 1977693Notes

Reaction equation

HRID 1977693 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:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[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:13]([O:21][CH2:22][CH3:23])=[O:20])[CH3:19]

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

9.13 g (55 mM) of 3,4-Dimethoxybenzaldehyde (veratraldehyde) was heated in 100 ml of benzene together with 8.00 mg (50 mM) of diethyl malonate, 0.29 ml of acetic acid, and 0.74 ml of piperidine in an apparatus equipped with a water separation tube (i.e., Dean Stark tube) until 50 mM water was separated. The benzene solution was washed with water and was dried over anhydrous magnesium sulfate. After being dried, the benzene was evaporated in vacuo to obtain 15.40 g crude product. The crude product obtained here had a sufficient purity even without purification, thus could be used as it was in the following step.

Workup

  1. customwas separated
  2. washThe benzene solution was washed with water
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customAfter being dried
  5. customthe benzene was evaporated in vacuo
  6. customto obtain 15.40 g crude product

Sources & evidence

ORD record
ord-c333055e3d12404db6b0ff9f4ee6f81a
Source dataset
uspto-grants-2001_05
Patent number
US06235739B1

Reaction notes

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