Water → HCID 12769821, compound

HRID 26677Notes

Reaction equation

HRID 26677 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:17])[CH2:15][OH:16])=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)[CH3:2].CC(C)=[O:20].OS(O)(=O)=O.O=[Cr](=O)=O.O>CC(C)=O>[CH2:1]([C:3]1[O:4][C:5]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:17])[C:15]([OH:20])=[O:16])=[CH:10][C:6]=2[C:7](=[O:9])[CH:8]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 127698102-Ethyl-6-(1-hydroxypropan-2-yl)-4H-1-benzopyran-4-oneHCID 131709961Jones' reagent

Product 1

HCID 12769821HCID 12769821, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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°.

Workup

  1. extractionthe mixture was extracted with chloroform (4×70 ml)
  2. extractionThe combined chloroform phases were extracted with saturated sodium bicarbonate solution (4×30 ml)
  3. washwashed with chloroform (100 ml)
  4. extractionThe precipitated product was extracted with chloroform (3×100 ml)
  5. dry with materialthe combined extracts dried over magnesium sulphate
  6. customAfter removing solvent
  7. customthe product was recrystallised from benzene/hexane (1;1)

Sources & evidence

ORD record
ord-040e02245ccf4febaf7f5fc948a20887
Source dataset
uspto-grants-1979_04
Patent number
US04151179

Reaction notes

Loading…