Ethanol → 2-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid ethyl ester

HRID 1733012Notes

Reaction equation

HRID 1733012 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([Cl:13])[CH:10]=[N:9]1.S(=O)(=O)(O)O.[CH2:24](O)[CH3:25]>>[CH2:24]([O:16][C:15](=[O:17])[CH:14]([C:4]1[CH:5]=[CH:6][C:7]([N:8]2[CH:12]=[C:11]([Cl:13])[CH:10]=[N:9]2)=[C:2]([Cl:1])[CH:3]=1)[CH3:18])[CH3:25]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 203034102-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid

Product 1

HCID 539945502-[3-Chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid ethyl esterYield 83%

Procedure

14.25 g (50 mmoles) of 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid, 150 ml of ethanol and 7 g of concentrated sulfuric acid are heated to the boil for 10 hours. Concentration is effected, followed by pouring onto ice water, extracting with diethyl ether, washing of the organic solution with sodium hydrogen carbonate solution, drying the organic solution and distilling it to obtain 12.4 g (83% of theory) of 2-[3-chloro-4-(4-chloropyrazol-1-yl)phenyl]propionic acid ethyl ester (b.p. 134° C./3·10-2 mm Hg).

Workup

  1. concentrationConcentration
  2. additionby pouring onto ice water
  3. extractionextracting with diethyl ether
  4. washwashing of the organic solution with sodium hydrogen carbonate solution
  5. customdrying the organic solution
  6. distillationdistilling it

Sources & evidence

ORD record
ord-9f94eab0f9fa4865b5610f639d867260
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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