Water → HCID 11311588, compound

HRID 398761Notes

Reaction equation

HRID 398761 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[C:12]([O:19][CH3:20])(=[O:18])[CH2:13][C:14]([O:16][CH3:17])=[O:15].O>C1C=CC=CC=1.C(O)(=O)C.N1CCCCC1>[CH3:17][O:16][C:14](=[O:15])[C:13](=[CH:7][C:6]1[CH:1]=[CH:2][C:3]2[O:11][CH2:10][O:9][C:4]=2[CH:5]=1)[C:12]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 3

HCID 962WaterHCID 7943Dimethyl malonateHCID 8438Piperonal

Product 1

HCID 11311588HCID 11311588, compoundYield 84.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of piperonal (15.0 g, 0.1 mol), dimethyl malonate (13.4 g, 0.1 mol), acetic acid (0.32 g, 5.3 mmol) and piperidine (0.43 g, 5.0 mmol) in benzene (200 ml) was stired and refluxed for 6 h with azeotropic distillation of H2O. The solvent was then removed at reduced pressure and the residue dissolved in ethyl acetate (100 ml). This solution was then extracted with 5% HCl (1X, 50 ml), then 5% Na2 CO3 (1X, 50 ml) followed by extraction with saturated aqueous NaCl (1x, 50 ml). The organic layer was dried (MgSO4), filtered and the solvent removed at reduced pressure to give a clear light oil (22.4 g) which solidified in part on standing. The oil was removed (by pipet) and the residual solid (18.3 g) recrystallized from ethanol (1X) to give 14.6 g (55%) of (a) as a crystalline white solid; mp 77°-74°.

Workup

  1. customThe solvent was then removed at reduced pressure
  2. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  3. extractionThis solution was then extracted with 5% HCl (1X, 50 ml)
  4. extraction5% Na2 CO3 (1X, 50 ml) followed by extraction with saturated aqueous NaCl (1x, 50 ml)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-1256309fa66c4856b69b32c41dcc0103
Source dataset
uspto-grants-1998_10
Patent number
US05817653

Reaction notes

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