Malonic Acid → HCID 10496253, compound

HRID 1815463Notes

Reaction equation

HRID 1815463 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=O.C(O)(=O)[CH2:19][C:20]([OH:22])=[O:21].N1CCCCC1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1/[CH:12]=[CH:19]/[C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 10636680HCID 10636680, compound

Product 1

HCID 10496253HCID 10496253, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the aldehyde (1.50 g, 5.3 mmol) from Example 1A, malonic acid (1.21 g, 11.6 mmol), piperidine (78.6 μL, 0.80 mmol) in 8.0 mL of anhydrous pyridine was heated at 110° C. for 2 hours. Gas evolution ceased during this period. Pyridine was then removed under vacuum. Water and 3N aq. HCl were then added with stirring. The desired cinnamic acid was then collected through filtration, washed with cold water and dried in a vacuum oven overnight to give 1.56 g (4.8 mmol, 91%) of white solid.

Workup

  1. waitGas evolution ceased during this period
  2. customPyridine was then removed under vacuum
  3. additionWater and 3N aq. HCl were then added
  4. filtrationThe desired cinnamic acid was then collected through filtration
  5. washwashed with cold water
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-7dd9530ab44e468baa2c22dae7650dc1
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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