Hydrochloric Acid → 2'-Benzyloxy-6'-hydroxy-4-methylchalcone

HRID 230870Notes

Reaction equation

HRID 230870 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16](=[O:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:21]1([CH3:29])[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1.Cl>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:10]=1[C:16](=[O:18])[CH:17]=[CH:29][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 77254-MethylbenzaldehydeHCID 14797Potassium HydroxideHCID 27751871-[2-(Benzyloxy)-6-hydroxyphenyl]ethan-1-one

Product 1

HCID 671363262'-Benzyloxy-6'-hydroxy-4-methylchalcone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2′-benzyloxy-6′-hydroxyacetophenone (0.5 g) in ethanol (10 mL)-water (3 mL) was added potassium hydroxide (1.39 g), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added p-tolualdehyde (0.37 mL), and the mixture was stirred at room temperature for 45 minutes. The reaction mixture was acidified by addition of 2 mol/L hydrochloric acid (12.5 mL), and the precipitated crystals were collected by filtration. The crystals were washed with water and dried under reduced pressure to give the title compound (0.69 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 45 minutes
  2. filtrationthe precipitated crystals were collected by filtration
  3. washThe crystals were washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-1e42d88d3045493d9652b4c0475eb92d
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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