Hydrochloric Acid → 3-hydroxy-2-(5-hydroxypentyl)chromen-4-one

HRID 1282251Notes

Reaction equation

HRID 1282251 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:12][C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8]1.Cl.C([O:24]N=O)CC(C)C>C(O)C>[OH:24][C:12]1[C:11](=[O:13])[C:10]2[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=2[O:8][C:7]=1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 10988187HCID 10988187, compound

Product 1

HCID 41574273-hydroxy-2-(5-hydroxypentyl)chromen-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3-dihydro-2-(5-hydroxypentyl)-4H-1-benzopyran-4-one (0.23 g) is dissolved in ethanol 95% (5 ml), and the solution is refluxed under stirring. HCl (6.2 ml) and isoamylnitrite (1.2 ml) are then added drop by drop. Stirring and heating are then stopped and the reaction mixture is allowed to stand for ca. 1 hour. The solvent is evaporated, water is then added and the product extracted with diethyl ether. The ethereal phase is dried by addition of anhydrous Na2SO4. After filtration and evaporation of the solvent an oil is obtained which is purified by chromatography with silica gel column and the mixture diethyl ether:methanol 98:2 as the eluent. 3-hydroxy-2-(5-hydroxypentyl)-4H-1-benzopyran-4-one (99.2 mg) is obtained. By crystallisation in cycloesane or diethyl ether the product in crystalline form is obtained (m.p.=111-112° C.).

Workup

  1. temperaturethe solution is refluxed
  2. stirringStirring
  3. temperatureheating
  4. customThe solvent is evaporated
  5. additionwater is then added
  6. extractionthe product extracted with diethyl ether
  7. dry with materialThe ethereal phase is dried by addition of anhydrous Na2SO4
  8. filtrationAfter filtration and evaporation of the solvent an oil
  9. customis obtained which
  10. customis purified by chromatography with silica gel column

Sources & evidence

ORD record
ord-1e2a0832466c49a69e7cebabfe63c7fe
Source dataset
uspto-grants-2002_09
Patent number
US06455578B1

Reaction notes

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