Hydrochloric Acid → HCID 13288097, compound

HRID 1981919Notes

Reaction equation

HRID 1981919 reaction equation
[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:17])[C:15]=1[CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[C:18]([OH:20])=[O:19])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH2:32][OH:33].Cl>CN(C)C=O>[CH2:1]([O:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]1[O:7][C:8]2[C:13]([C:14](=[O:17])[C:15]=1[CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[C:18]([O:20][CH2:31][CH2:32][OH:33])=[O:19])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 132881092-(2-Ethoxyphenyl)-3-methyl-4-oxo-4H-1-benzopyran-8-carboxylic acid

Product 1

HCID 13288097HCID 13288097, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One gram of 2'-ethoxy-3-methylflavone-8-carboxylic acid prepared by the same way as Example 1 is dissolved in 30 ml of dimethyl formamide, 0.5 gram of anhydrous potassium carbonate is added thereto, 2 grams of ethylene bromohydrin is dropped thereinto with stirring, and the mixture is stirred at 50° C. for four hours. Then it is poured into ice water, the mixture is neutralized with 10% hydrochloric acid, extracted with ethyl acetate, the extract is washed with water, dried with anhydrous magnesium sulfate, the solvent is evaporated therefrom, and the residue is recrystallized from a mixture of benzene and n-hexane to give 0.8 gram of beta-hydroxyethyl 2'-ethoxy-3-methylflavone-8-carboxylate, colorless needles, melting point 143° to 144.5° C.

Workup

  1. stirringthe mixture is stirred at 50° C. for four hours
  2. extractionextracted with ethyl acetate
  3. washthe extract is washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customthe solvent is evaporated
  6. customthe residue is recrystallized from a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-ffe9e69e1d504aa9a4cb4ccd8a8cacec
Source dataset
uspto-grants-1986_06
Patent number
US04594345

Reaction notes

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