Toluene → 3-(4-Chlorocinnamoyl)-propionic acid

HRID 2131

Reaction equation

HRID 2131 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([OH:17])(=[O:16])[CH2:11][CH2:12][C:13]([CH3:15])=[O:14].N1CCCCC1.C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:15][C:13]([CH2:12][CH2:11][C:10]([OH:17])=[O:16])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 77264-ChlorobenzaldehydeHCID 8082PiperidineHCID 11579Levulinic Acid

Product 1

HCID 543510133-(4-Chlorocinnamoyl)-propionic acidYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dry 250 ml flask equipped with a magnetic stirrer, Dean-Stark trap, and reflux condenser was charged 15 g of 4-chlorobenzaldehyde, 12.4 g levulenic acid, 5.7 ml of piperidine, and 100 ml of toluene. The reaction was refluxed for 3 hours, after which no water was observed to azeotrope from the solution. The reaction was cooled and stripped to yield a reddish-brown liquid which was triturated with hexane to yield 11.2 g of product as a yellow solid.

Workup

  1. customTo a dry 250 ml flask equipped with a magnetic stirrer
  2. temperatureDean-Stark trap, and reflux condenser
  3. temperatureThe reaction was refluxed for 3 hours
  4. temperatureThe reaction was cooled
  5. customto yield a reddish-brown liquid which
  6. customwas triturated with hexane

Sources & evidence

ORD record
ord-41e667fc94ef4b21b0e687948a96209d
Source dataset
uspto-grants-1998_03
Patent number
US05728698

Linked notes

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