1,2-Epoxybutane → 6-Carboxy2'-(2-hydroxy-butoxy)-flavone

HRID 2083012

Reaction equation

HRID 2083012 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])=[CH:9][C:8]2=[O:22])([O:3]C)=[O:2].[O:23]1[CH:25]([CH2:26][CH3:27])[CH2:24]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:24][CH:25]([OH:23])[CH2:26][CH3:27])=[CH:9][C:8]2=[O:22])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 78341,2-EpoxybutaneHCID 66854Benzyltrimethylammonium hydroxideHCID 124078666-Carbomethoxy-2'-hydroxy-flavone

Product 1

HCID 213250166-Carboxy2'-(2-hydroxy-butoxy)-flavoneYield 39.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture consisting of 6-carbomethoxy-2'-hydroxy-flavone (10 g), obtained according to the method described in Example 2, and 1,2-epoxy-butane (6 g) and benzyl-trimethylammonium hydroxide (0.5 ml) in dioxane (40 ml) was kept at reflux temperature for 48 hours. After cooling, dilution with water, and extraction with ethylacetate, the organic phase was washed with potassium carbonate 5% and water. The solution was evaporated to dryness, and the resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95% at reflux temperature for an hour. After acidification with acetic acid, concentration under vacuum, dilution with water, filtration and double crystallisation from ethanol, 6-carboxy-2'-(2-hydroxy-butoxy)-flavone (4.7 g) was obtained.

Workup

  1. customobtained
  2. temperatureat reflux temperature for 48 hours
  3. temperatureAfter cooling
  4. extractiondilution with water, and extraction with ethylacetate
  5. washthe organic phase was washed with potassium carbonate 5% and water
  6. customThe solution was evaporated to dryness
  7. additionthe resulting product was treated with the stoichiometric quantity of a solution of potassium hydroxide 1% in ethanol 95%
  8. temperatureat reflux temperature for an hour
  9. concentrationAfter acidification with acetic acid, concentration under vacuum, dilution
  10. filtrationwith water, filtration and double crystallisation from ethanol

Sources & evidence

ORD record
ord-d1eac691fa524322bdf308eccb6e5ef7
Source dataset
uspto-grants-1978_04
Patent number
US04083953

Linked notes

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