Water → 4-[2-Chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde

HRID 1922052Notes

Reaction equation

HRID 1922052 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9](O)[CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].S(Cl)([Cl:23])=O.O>C(Cl)(Cl)Cl>[Cl:23][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1)[CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 115507874-[2-(5-Ethyl-2-pyridinyl)-2-hydroxyethoxy]benzaldehyde

Product 1

HCID 713792474-[2-Chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzaldehydeYield 76.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 5 g (0.018 mol) 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde dissolved in chloroform was added 2.63 g (0.022 mol) thionyl chloride at 55-60° C. Reaction mixture was refluxed for 1 hr. Progress of the reaction was monitored by TLC and after completion of reaction, subsequent work-up in alkaline water yielded 4 g (75%) of the desired product.

Workup

  1. customReaction mixture
  2. temperaturewas refluxed for 1 hr

Sources & evidence

ORD record
ord-bac1c626bb5c47a6a69974a0b96b6fdd
Source dataset
uspto-grants-2012_05
Patent number
US08173816B2

Reaction notes

Loading…