Hydrochloric Acid → Licochalcone A

HRID 1603172Notes

Reaction equation

HRID 1603172 reaction equation
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:20]=[C:19]([OH:21])[C:18]([C:22]([CH3:26])([CH3:25])[CH:23]=[CH2:24])=[CH:17][C:14]=1[CH:15]=O.Cl.O>C(O)C>[CH3:26][C:22]([C:18]1[CH:17]=[C:14](/[CH:15]=[CH:1]/[C:2]([C:4]2[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=2)=[O:3])[C:13]([O:12][CH3:11])=[CH:20][C:19]=1[OH:21])([CH:23]=[CH2:24])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 74694'-HydroxyacetophenoneHCID 12153345HCID 12153345, compound

Product 1

HCID 5318998Licochalcone AYield 35.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 150 mg (1.1 mmol) of 4-hydroxyacetophenone and 220 mg (1.0 mmol) of 2-methoxy4-hydroxy-5-(1,1-dimethylprop-2-enyl)benzaldehyde in 3 ml of ethanol was left on an ice bath, and 1.1 ml of ethanol saturated with dry hydrogen chloride was added. The solution was left for 2 hours and poured into 10 ml of water. The mixture was concentrated in vacuo and extracted with two 10 ml portions of ethyl acetate, and the extract was dried and concentrated in vacuo to give 281 mg of an oil from which 119 mg of licochalcone A was isolated by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 23 g) using petroleum ether-ethyl acetate (1:1, 1000 ml) as an eluent.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with two 10 ml portions of ethyl acetate
  3. customthe extract was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7278627c34e4825a5e4065ed1d134c5
Source dataset
uspto-grants-1999_11
Patent number
US05985935

Reaction notes

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