Sulfuric Acid → 1-(o-Chlorophenyl)-3-(p-fluorophenyl)-2-formylprop-1-ene

HRID 654842Notes

Reaction equation

HRID 654842 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[OH-].[Na+].[F:12][C:13]1[CH:22]=[CH:21][C:16]([CH2:17][CH2:18][CH:19]=[O:20])=[CH:15][CH:14]=1.S(=O)(=O)(O)O>CO>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:18]([CH:19]=[O:20])[CH2:17][C:16]1[CH:21]=[CH:22][C:13]([F:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 69962-ChlorobenzaldehydeHCID 14798Sodium HydroxideHCID 101977823-(4-Fluorophenyl)propanal

Product 1

HCID 544302061-(o-Chlorophenyl)-3-(p-fluorophenyl)-2-formylprop-1-ene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

71.7 g (0.51 mol) of 2-chlorobenzaldehyde are added to a solution of 4 g of 50% strength sodium hydroxide solution in 300 ml of methanol while cooling, at a rate such that the temperature does not exceed 20° C. 70.0 g (0.46 mol) of p-fluorodihydrocinnamaldehyde are then added dropwise at 25°-30° C. in the course of 4 hours. Stirring is continued for one hour at 30° C., the mixture is neutralized with dilute sulfuric acid and evaporated down and the residue is distilled.

Workup

  1. temperaturewhile cooling, at a rate such that the temperature
  2. customdoes not exceed 20° C
  3. customevaporated down
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-601a760a7c11495bba6b6038f6d61acb
Source dataset
uspto-grants-1992_07
Patent number
US05134167

Reaction notes

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