Methanol → 2-Hydroxychalcone

HRID 2101225Notes

Reaction equation

HRID 2101225 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:10][OH:11]>>[OH:11][C:10]1[CH:2]=[CH:1][CH:4]=[CH:5][C:6]=1[CH:7]=[CH:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

3

Reactant 2

HCID 887MethanolHCID 7410Acetophenone

Product 1

HCID 977652-Hydroxychalcone

Procedure

The previous product was mixed with acetophenone (2 g) suspended in methanol at −10° C. and stirred for 5 hr at room temperature. After neutralization with 5% hydrochloric acid solution, the product was extracted with 200 Ml of ethylacetate. The extracted organic phase was dried with anhydrous magnesium sulfate, and resulting 1-phenyl-3-(2-methoxymethyloxyphenyl)-prophenone was hydrolyzed with dilute alkaline solution. The reaction mixture was extracted with 200 Ml of ethylacetate. Extracted organic phase is dried with anhydrous magnesium sulfate and evaporated under vacuum. About 0.9 g of white solid (1-phenyl-3-(2-hydroxyphenyl)prophenone was obtained and subjected to silica gel column chromatography (5×3 cm, Merk). After being eluted with n-hexane:ethylacetate (v/v, 1:7), 0.7 g of purified compound was recovered and identified as follows:

Workup

  1. extractionAfter neutralization with 5% hydrochloric acid solution, the product was extracted with 200 Ml of ethylacetate
  2. dry with materialThe extracted organic phase was dried with anhydrous magnesium sulfate
  3. customresulting 1-phenyl-3-(2-methoxymethyloxyphenyl)-prophenone
  4. additionwith dilute alkaline solution
  5. extractionThe reaction mixture was extracted with 200 Ml of ethylacetate
  6. dry with materialExtracted organic phase is dried with anhydrous magnesium sulfate
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-ff840c3eef184e24890a7e5770e0b191
Source dataset
uspto-grants-2009_08
Patent number
US07572831B2

Reaction notes

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