Reaction #54955

Reaction equation

2-(2-Ethyl-4-oxo-4H-1-benzopyran-6-yl)propan-1-ol

Jones Reagent

Water

→

solid

2-(2-Ethyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid

Solvents

acetone

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with chloroform (4×70 ml)
2. 2
   ExtractionThe combined chloroform phases were extracted with saturated sodium bicarbonate solution (4×30 ml)
3. 3
   Washwashed with chloroform (100 ml)
4. 4
   ExtractionThe precipitated product was extracted with chloroform (3×100 ml)
5. 5
   Dryingthe combined extracts dried over magnesium sulphate
6. 6
   OtherAfter removing solvent
7. 7
   Otherthe product was recrystallised from benzene/hexane (1;1)

Procedure

2-(2-Ethyl-4-oxo-4H-1-benzopyran-6-yl)propan-1-ol (3.0 g; 0.0129 mol) was dissolved in acetone (20 ml) and Jones Reagent (Example 2) was slowly added until the solution attained a permanent brown colour. Water (100 ml) was added and the mixture was extracted with chloroform (4×70 ml). The combined chloroform phases were extracted with saturated sodium bicarbonate solution (4×30 ml). The aqueous phases were combined, washed with chloroform (100 ml) and then acidified with concentrated hydrochloric acid. The precipitated product was extracted with chloroform (3×100 ml) and the combined extracts dried over magnesium sulphate. After removing solvent, the product was recrystallised from benzene/hexane (1;1) to yield a pale yellow amorphous solid (1.4 g) mp 128°-128.5°.

Source