Acetone → HCID 23459802, compound

HRID 2287200Notes

Reaction equation

HRID 2287200 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8]2.CC(C)=[O:27]>O.S(=O)(=O)(O)O.[O-2].[O-2].[O-2].[Cr+6]>[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=[O:27]

Participants

6

Reactant 2

HCID 180Acetone2×HCID 23459804HCID 23459804, compound

Product 1

HCID 23459802HCID 23459802, compound

Reagents, catalysts & solvents 3

HCID 10219390chromium (VI) trioxideCatalystHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

Methyl 6,7,8,9-tetrahydro-5-methoxy-4-oxo-10-propyl-4H-naphtho-[2,3-b]pyran-2-carboxylate (81.4 g; 0.25 mole) was dissolved in acetone (1 l) and stirred rapidly while adding a solution of chromium trioxide (220 g) in water (830 ml) and concentrated sulphuric acid (190 ml), adding at such a rate that the acetone refluxed gently. The mixture was then stirred at room temperature overnight, poured into water (1 l) and extracted into chloroform (3×). The organic fractions were combined, dried (sodium sulphate) and evaporated to give a yellow oil which was submitted to high pressure liquid chromatography (HPLC) to separate the components.

Workup

  1. temperaturerefluxed gently
  2. stirringThe mixture was then stirred at room temperature overnight
  3. extractionextracted into chloroform (3×)
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. customto give a yellow oil which
  7. customto separate the components

Sources & evidence

ORD record
ord-298106ad005a4165b4b5775cca59e488
Source dataset
uspto-grants-1981_05
Patent number
US04269854

Reaction notes

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