Acetic Acid → Diethyl (2,6-dimethoxybenzylidene)malonate

HRID 326697

Reaction equation

HRID 326697 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:12][O:13][C:14]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:15]=1[CH:16]=O.N1CCCCC1.C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH3:23][O:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:14]([O:13][CH3:12])[C:15]=1[CH:16]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 12514881Diethyl (2,6-dimethoxybenzylidene)malonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 1.52 ml of diethyl malonate, 1.66 g of 2,6-dimethoxybenzaldehyde, 0.1 ml of piperidine, 0.11 ml of glacial acetic acid and 100 ml of toluene was boiled at 110° C. on a water separator for 3.5 hours. The solution was extracted with 10% NaHCO3 solution and back-washed with saturated NaCl solution. The organic phase was dried, filtered under suction and evaporated under reduced pressure. There were obtained 2.8 g of diethyl (2,6-dimethoxybenzylidene)malonate, as a dark yellow oil.

Workup

  1. customfor 3.5 hours
  2. extractionThe solution was extracted with 10% NaHCO3 solution
  3. washback-washed with saturated NaCl solution
  4. customThe organic phase was dried
  5. filtrationfiltered under suction
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9ac6537c309a41c787eebe8636cabbc8
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Linked notes

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