Hydrochloric Acid → HCID 53404339, compound

HRID 929328Notes

Reaction equation

HRID 929328 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=O.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14].N1CCCCC1.Cl>O.N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[CH:12][C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 53404339HCID 53404339, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

3-Methyl-4-hydroxybenzaldehyde (794 mg, 5.83 mmol), malonic acid (911 mg, 8.75 mmol) and piperidine (144 μl) were added to pyridine (5 ml), and the mixture was stirred at 60° C. for 22 hours under an argon atmosphere. The reaction mixture was allowed to cool to room temperature, and water (20 ml) was added. 6N Hydrochloric acid was added to allow precipitation of a solid. The precipitated solid was collected by filtration, and the filtrate was washed with water and dried under reduced pressure. The obtained solid was recrystallized from diethylether-n-hexane to give 3-methyl-4-hydroxycinnamic acid (872 mg, yield 84.0%) as crystals.

Workup

  1. temperatureto cool to room temperature
  2. customprecipitation of a solid
  3. filtrationThe precipitated solid was collected by filtration
  4. washthe filtrate was washed with water
  5. customdried under reduced pressure
  6. customThe obtained solid was recrystallized from diethylether-n-hexane

Sources & evidence

ORD record
ord-a5dd8ae948f546d5aa1434cb66a44ab6
Source dataset
uspto-grants-2016_03
Patent number
US09295624B2

Reaction notes

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