Pyridine → 4-chlorophenyl propionate

HRID 1941007Notes

Reaction equation

HRID 1941007 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.C1(C)C=CC=CC=1.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:22](=[O:25])[CH2:23][CH3:24])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 46844-ChlorophenolHCID 62324Propionyl chloride

Product 1

HCID 2433484-chlorophenyl propionateYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a mixture of p-chlorophenol (20.0 g, 156 mmol), pyridine (14.8 g, 187 mmol), and toluene (150 ml), propionic acid chloride (17.3 g, 187 mmol) was added dropwise, and the resultant mixture was stirred for 1 hour at room temperature. Water (150 ml) was added and the aqueous layer was discarded. The organic layer was concentrated and distilled under reduced pressure (bp. 73°-76° C./0.2 mmHg), thereby obtaining a propionic acid-p-chlorophenyl ester (25.6 g, 138 mmol, 89%).

Workup

  1. additionwas added dropwise
  2. concentrationThe organic layer was concentrated
  3. distillationdistilled under reduced pressure (bp. 73°-76° C./0.2 mmHg)

Sources & evidence

ORD record
ord-58afd37664d544ebae1382358512f9a8
Source dataset
uspto-grants-1997_12
Patent number
US05702691

Reaction notes

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