Benzoic Acid → HCID 21082449, compound

HRID 347291Notes

Reaction equation

HRID 347291 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[C:14]([C:13]([O:20][CH3:21])=[O:19])[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 7943Dimethyl malonateHCID 8082PiperidineHCID 691752,4-Dimethoxybenzaldehyde

Product 1

HCID 21082449HCID 21082449, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4-Dimethoxybenzaldehyde (10.0 g, 0.060 mol), dimethyl malonate (9.5 g, 0.072 mol), piperidine (1.5 g, 0.017 mol), benzoic acid (1.8 g, 0.015 mol) and 100 mL of toluene are stirred at reflux for 5.5 hours under a Dean Stark trap to remove water. After cooling to room temperature, the reaction mixture is partitioned between ethyl acetate and water. The organic layer is washed with 10% hydrochloric acid, water and brine. The resulting solution is dried over anhydrous magnesium sulfate and then concentrated to yield 17.8 g of an orange syrup which is purified by chromatography on silica gel (2:1, heptane:ethyl acetate) to provide 12.8 g of the title compound as a pale yellow solid melting at 71–73° C.

Workup

  1. temperatureat reflux for 5.5 hours under a Dean Stark trap
  2. customto remove water
  3. customthe reaction mixture is partitioned between ethyl acetate and water
  4. washThe organic layer is washed with 10% hydrochloric acid, water and brine
  5. dry with materialThe resulting solution is dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2dd8367186004890a39c6d3cda5b5602
Source dataset
uspto-grants-2007_02
Patent number
US07173128B2

Reaction notes

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