Benzaldehyde → 5′-Chloro-2′-hydroxychalcone

HRID 1719513Notes

Reaction equation

HRID 1719513 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].OS(O)(=O)=O>O>[O:3]=[C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:1]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 740613-Chloro-6-hydroxyacetophenone

Product 1

HCID 1210655′-Chloro-2′-hydroxychalconeYield 74.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

34.1 g of 5-chloro-2-hydroxyacetophenone and 22 g of benzaldehyde were added to a mixture of 180 ml of H2O and 37 g of 50% strength sodium hydroxide solution at room temperature. The mixture was heated to 55°-60° C., with thorough stirring, and was stirred at this temperature for about 1 hour. It was then rendered weakly acid with 25% strength H2SO4 (about 100 ml), with thorough cooling, and the precipitate was filtered off with suction, washed thoroughly with H2O and recrystallized from a 9:1 mixture of methanol and acetone to give 38.7 g of 3-oxo-1-phenyl-3-(2'-hydroxy-5'-chlorophenyl)-propene of melting point 88°-90° C.

Workup

  1. temperatureThe mixture was heated to 55°-60° C., with thorough stirring
  2. filtrationwith thorough cooling, and the precipitate was filtered off with suction
  3. washwashed thoroughly with H2O
  4. customrecrystallized from a 9:1 mixture of methanol and acetone

Sources & evidence

ORD record
ord-d6f55efc0d2c440b8030d6e1df5239a6
Source dataset
uspto-grants-1985_09
Patent number
US04540697

Reaction notes

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