Hydrochloric Acid → 2'-Hydroxy-4'-iodo-3,4,5-trimethoxy-chalcone

HRID 1819532Notes

Reaction equation

HRID 1819532 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][C:5]=1[OH:11])=[O:3].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH:17]=O.[OH-].[K+].Cl>C(O)C.O>[OH:11][C:5]1[CH:6]=[C:7]([I:10])[CH:8]=[CH:9][C:4]=1[C:2](=[O:3])[CH:1]=[CH:17][C:16]1[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([O:13][CH3:12])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 68583,4,5-TrimethoxybenzaldehydeHCID 14797Potassium HydroxideHCID 124303391-(2-Hydroxy-4-iodophenyl)ethanone

Product 1

HCID 688868382'-Hydroxy-4'-iodo-3,4,5-trimethoxy-chalconeYield 126.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirring suspension of 29 (0.55 g, 2.1 mmol) and 3,4,5-trimethoxy-benzaldehyde (0.66 g, 3.4 mmol, 1.6 equ) in ethanol (10 ml) was added potassium hydroxide (0.25 g, 4.5 mmol, 2.1 equ). The reaction mixture was stirred for 119 hours then diluted with water, acidified (1N HCl) and extracted with ethyl acetate (3×70 ml). The combined organic layers were then washed with saturated aqueous sodium bicarbonate (50 ml), saturated brine (50 ml), 10% sodium bisulfite solution (3×50 ml) and then saturated brine (50 ml) again. The organic layer was then dried (MgSO4) and concentrated in vacuo to give a yellow solid (1.17 g). This solid was heated in methanol, and the undissolved solid collected. The filtrate was concentrated and then heated in methanol again. More undissolved solid was collected. Undissolved solid is 32 (0.50 g, 54%).

Workup

  1. extractionextracted with ethyl acetate (3×70 ml)
  2. washThe combined organic layers were then washed with saturated aqueous sodium bicarbonate (50 ml), saturated brine (50 ml), 10% sodium bisulfite solution (3×50 ml)
  3. dry with materialThe organic layer was then dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71709d0a59f0459a9783de1bf93f87a7
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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