Hydrochloric Acid → 2'-Hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalcone

HRID 2286189Notes

Reaction equation

HRID 2286189 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:14])[CH3:13].[CH3:15][O:16][CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.[OH-].[Na+].Cl>C(O)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[C:12](=[O:14])[CH:13]=[CH:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][O:16][CH3:15])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66654XanthoxylinHCID 2500744-(Methoxymethoxy)benzaldehyde

Product 1

HCID 539872122'-Hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalconeYield 28.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution containing 1.57 g (8 m moles) of 2'-hydroxy-4',6'-dimethoxyacetophenone and 1.33 g (8 m moles) of 4-(methoxymethoxy)benzaldehyde in 3 ml of ethanol, there were added 30 ml of 15% by volume aqueous sodium hydroxide. After being stirred at room temperature for 2 days, the mixture was poured into 70 ml of ice-water. The pH was adjusted to 7 by adding hydrochloric acid, and the mixture was extracted with two 150 ml portions of dichloromethane. The combined extracts were washed with water, dried over sodium sulfate and then evaporated. The oily residue was crystallized from methanol to yield 780 mg of 2'-hydroxy-4',6'-dimethoxy-4-(methoxymethoxy)chalcone as yellow needles: mp 104.5° C.

Workup

  1. extractionthe mixture was extracted with two 150 ml portions of dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe oily residue was crystallized from methanol

Sources & evidence

ORD record
ord-6cc84e0c64a6491fae4abe95fe8c3816
Source dataset
uspto-grants-1982_04
Patent number
US04327088

Reaction notes

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