Acetic Acid → HCID 54520662, compound

HRID 1587009Notes

Reaction equation

HRID 1587009 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:19][CH3:20])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16].C(O)(=O)C.O>C1C=CC=CC=1.N1CCCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[C:14]([C:15]([CH3:17])=[O:16])[C:13]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 7757Methyl acetoacetateHCID 8419Veratraldehyde

Product 1

HCID 54520662HCID 54520662, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 54.8 g (0.33 mol) 3,4-dimethoxybenzaldehyde and 34.8 mg (0.3 mol) methyl acetoacetate in 20 ml benzene, were added dropwise 1.02 g (12 mmol) piperidine and 3.66 g (61 mmol) acetic acid in that order, and water was removed from the mixture by heating in a Dean-Stark apparatus until water was no longer distilled off. The solvents were distilled off from the reaction mixture, and the oil thus left was allowed to stand for five days. The crystals which separated out were collected by filtration, giving 41.1 g (52%) of methyl 2-(3,4-dimethoxy-benzylidene)acetoacetate as yellow crystals. M.P.: 93°-95° C.

Workup

  1. customwas removed from the mixture
  2. temperatureby heating in a Dean-Stark apparatus until water
  3. distillationwas no longer distilled off
  4. distillationThe solvents were distilled off from the reaction mixture
  5. waitthe oil thus left
  6. customThe crystals which separated out
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-a624e0b1972a424c94d74cec7928f6f6
Source dataset
uspto-grants-1993_06
Patent number
US05216172

Reaction notes

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