Hydrochloric Acid → 4'-Methoxyacetophenone

HRID 1603173Notes

Reaction equation

HRID 1603173 reaction equation
COC1C=C(OC)C=CC=1C=[CH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22]C=C)=[CH:17][CH:16]=1)=[O:14].CC(C1C=CC(OCC=C)=CC=1)=O.COC1C=C(OC)C=CC=1C=O.Cl>C(O)C>[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 691752,4-DimethoxybenzaldehydeHCID 959691-(4-(2-Propen-1-yloxy)phenyl)ethanoneHCID 545548812,4-Dimethoxy-4'-(2-propenyloxy)chalcone

Product 1

HCID 74764'-MethoxyacetophenoneYield 122.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Preparation of 2,4dimethoxy4'-prop-2-enyloxychalcone ##STR30## 0.88 g of 4-allyloxyacetophenone and 0.42 g of 2,4-dimethoxybenzaldehyde were dissolved in 3.5 ml of ethanol, and to the solution was added ethanol saturated with 3.5 ml of hydrogen chloride. The mixture was left at room temperature for 30 min during which time it turned heavily red. The solution was concentrated in vacuo and the residue chromatographed (column chromatography over silica gel 60 (Merck 0.0630-0.200 mm, 100 g), eluent toluene and toluene to which increasing amounts of ethyl acetate were added) to give 500 mg of 4-methoxyacetophenone and 471 mg of 2,4-dimethoxy-4'-prop-2-enyloxychone. The chalcone was recrystallized from petroleum ether-ethyl acetate to give 370 mg of slightly yellow crystals. For data, see Example 2.24.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue chromatographed
  3. temperature(column chromatography over silica gel 60 (Merck 0.0630-0.200 mm, 100 g), eluent toluene and toluene to which increasing amounts of ethyl acetate were added)

Sources & evidence

ORD record
ord-19b2f443f3e9415c9e512c01c3c4f70e
Source dataset
uspto-grants-1999_11
Patent number
US05985935

Reaction notes

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