Acetic Acid → HCID 68647810, compound

HRID 1162159Notes

Reaction equation

HRID 1162159 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]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#N.[NH:21]1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[C:16]([O:18][CH:19]([C:20]#[N:21])[CH2:6][C:5]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:17])[CH:15]=[CH2:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 8419Veratraldehyde

Product 1

HCID 68647810HCID 68647810, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
125 °C

Procedure

Add 3,4-dimethoxy benzaldehyde 26 g (0.16 mol), ethyl cyanoacetate 18 g (0.16 mol), piperidine 0.8 ml, acetic acid 2.4 g, and benzene 60 ml into 250 ml eggplant-shaped flask, increase temperature to 120-130° C. for intensive reflux, separate water with water separator, react for 12 h. Vacuum evaporate to remove benzene, pour ice water into the reaction solution to precipitate yellow solid, filter and dry to obtain pale yellow crystal VIII-b-2 41 g, with yield almost reaching theoretical value and m.p. 154-156° C. (reference value 156° C.).

Workup

  1. customseparate water with water separator
  2. customreact for 12 h
  3. customVacuum evaporate
  4. customto remove benzene
  5. additionpour ice water into the reaction solution
  6. customto precipitate yellow solid
  7. filtrationfilter
  8. customdry
  9. customto obtain pale yellow crystal VIII-b-2 41 g
  10. customwith yield almost
  11. customvalue and m.p. 154-156° C. (reference value 156° C.)

Sources & evidence

ORD record
ord-f47fbf1b13034c2591afff6032fe9456
Source dataset
uspto-grants-2010_10
Patent number
US07820692B2

Reaction notes

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