Acetic Acid → HCID 12766830, compound

HRID 1577678Notes

Reaction equation

HRID 1577678 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[C:15]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][C:5]=1[CH:6]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:15]([O:23][CH2:24][CH3:25])=[O:22])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 34343142,5-Diethoxybenzaldehyde

Product 1

HCID 12766830HCID 12766830, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

2,5-Diethoxybenzaldehyde (24 g., 0.124 mole) and diethyl malonate (20 g., 0.125 mole) are added to a solution of piperidine (3.0 g.) and glacial acetic acid (6 ml.) in benzene (160 ml.). The mixture is heated under reflux utilizing a Dean-Stark water separater until water ceased to be separated. After 8 hours of distillation 2.3 ml. of water out of a theoretical yield of 2.23 ml. are obtained and the reaction mixture cooled. The cooled reaction mixture is washed with aqueous hydrochloric acid (6 N, 70 ml.) water (70 ml.) and aqueous sodium bicarbonate (5% w/w, 50 ml.). The organic layer is separated, dried over magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield a yellow oil (42.7 g., 0.127 mole, 100%). Trituration with petroleum ether yields diethyl 2,5-Diethoxybenzylidenemalonate (38.4 g., 0.114 mole, 92%) m.p. (from petroleum ether) 52°-53° C. I.R.: 1720 cm- 1 mass spec m/e 336.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. customto be separated
  4. distillationAfter 8 hours of distillation 2.3 ml
  5. customare obtained
  6. temperaturethe reaction mixture cooled
  7. customThe cooled reaction mixture
  8. washis washed with aqueous hydrochloric acid (6 N, 70 ml.) water (70 ml.) and aqueous sodium bicarbonate (5% w/w, 50 ml.)
  9. customThe organic layer is separated
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customthe solvent removed under reduced pressure
  13. customto yield a yellow oil (42.7 g., 0.127 mole, 100%)

Sources & evidence

ORD record
ord-411643c350b9497c836c5f31ae94a8c0
Source dataset
uspto-grants-1981_09
Patent number
US04288608

Reaction notes

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