Pyridine → 4-chlorophenyl propionate

HRID 1417117Notes

Reaction equation

HRID 1417117 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 addeddropwise, 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 anddistilled 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. concentrationThe organic layer was concentrated anddistilled under reduced pressure (bp. 73°-76° C./0.2 mmHg)

Sources & evidence

ORD record
ord-d19e830ec19e4df5bc807f5bf50d8110
Source dataset
uspto-grants-1999_03
Patent number
US05876703

Reaction notes

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