Benzoic Acid → HCID 1811896, compound

HRID 2308995Notes

Reaction equation

HRID 2308995 reaction equation
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[C:9]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:6][C:5]([CH:7]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:9]([O:17][CH2:18][CH3:19])=[O:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 616635-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 1811896HCID 1811896, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 215 g (1.71 moles) sample of 5-methyl-2-thiophenecarboxaldehyde, 258 ml (1.71 moles) diethyl malonate, 25 ml piperidine, 0.52 g benzoic acid, and 1.5 L toluene were placed into a round bottom flask and heated to reflux for four hr. with azeotropic removal of water. The reaction was cooled and water was added. The toluene layer was washed with sodium bicarbonate solution. 3N hydrochloric acid, water, brine and dried (MgSO4). The solvent was evaporated in vacuo. The residue was washed with methylcyclohexane. The washings were collected, the solvent removed in vacuo and the residue was recrystallized from methylcyclohexane. The solid materials were combined to give 299.86 g of diethyl 2-[(5-methyl-2-thienyl)methylene]propanedioate, mp 53°-56° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for four hr
  3. customwith azeotropic removal of water
  4. temperatureThe reaction was cooled
  5. additionwater was added
  6. washThe toluene layer was washed with sodium bicarbonate solution
  7. dry with material3N hydrochloric acid, water, brine and dried (MgSO4)
  8. customThe solvent was evaporated in vacuo
  9. washThe residue was washed with methylcyclohexane
  10. customThe washings were collected
  11. customthe solvent removed in vacuo
  12. customthe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-a709cf0fa4a9462d9ca5daf93e0ec5e2
Source dataset
uspto-grants-1987_09
Patent number
US04692460

Reaction notes

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