6-Hydroxy-chroman-4-one Chemical Properties

Melting point:

129-131 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))

Boiling point:

372.4±42.0 °C(Predicted)

Density 

1.343±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.58±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C9H8O3/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-2,5,10H,3-4H2

InChIKey

HTKPIKIGEYFNBY-UHFFFAOYSA-N

SMILES

C1OC2=CC=C(O)C=C2C(=O)C1

6-Hydroxy-chroman-4-one Usage And Synthesis

Uses

6-Hydroxy-chroman-4-one is used in the preparation of novels parasite transmission blocking antimalarials targeting male gametes

Synthesis

(3) Preparation of 2,3-dihydro-6-hydroxychromen-4-one: 6-methoxychromen-dihydropyran-4-one (2.9 g, 0.0163 mol) was sequentially added to a mixed solution of glacial acetic acid (20 mL) and HBr (>40%, 20 mL), stirred and refluxed for 1 h. The reaction solution was then extracted with ethyl acetate. Upon completion of the reaction, the pH of the reaction solution was adjusted to 10-11 with KOH solution, and then the pH of the aqueous layer was adjusted to 2-3 with concentrated hydrochloric acid.Subsequently, the aqueous layer was extracted with ethyl acetate, and the organic layers were combined and dried with anhydrous Na2SO4. The dried organic layer was cooled and a black solid was precipitated. The solid was recrystallized with ethyl acetate to give 2.17 g of bright yellow crystals with a melting point of 142-144 °C and a yield of 81.2%.

References

[1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2773 - 2778
[2] Patent: US5641789, 1997, A
[3] Patent: US2008/103307, 2008, A1. Location in patent: Page/Page column 17
[4] Patent: US5322847, 1994, A
[5] Patent: EP641792, 1995, A1

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