Acetic Acid → HCID 16769096, compound

HRID 1637185Notes

Reaction equation

HRID 1637185 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:6][CH:5]=1.Cl.Cl[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C(O)(=O)C>C(O)C>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH2:17][O:3][C:4]2[CH:5]=[CH:6][C:7](/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 637542P-Coumaric Acid

Product 1

HCID 16769096HCID 16769096, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An aqueous solution of 2M NaOH (165 ml) was added to a solution of (E)-3-[4-hydroxyphenyl]-2-propenoic acid (16.4 g, 100 mmol) in ethanol (100 ml). The mixture was stirred for 10 minutes, and then 3-(chloromethyl)-pyridine hydrochloride (19.7 g, 120 mmol) was added in portions. The mixture was stirred for 20 hours, and the solvents were evaporated under reduced pressure. Water was added and the suspension heated to give a solution. To this solution was added acetic acid, and the resultant precipitate was filtered and recrystallised from methanol to give the title compound as a colourless solid (15.6 g).

Workup

  1. stirringThe mixture was stirred for 20 hours
  2. customthe solvents were evaporated under reduced pressure
  3. additionWater was added
  4. temperaturethe suspension heated
  5. customto give a solution
  6. filtrationthe resultant precipitate was filtered
  7. customrecrystallised from methanol

Sources & evidence

ORD record
ord-5badd08b35fb47c187dc626396133d54
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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