Acetate → HCID 12906159, compound

HRID 647056Notes

Reaction equation

HRID 647056 reaction equation
[CH3:1][C:2]1[C:3](=[O:22])[C:4]([CH:11]([OH:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8].C([O-])(=O)C.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)C>CC(C)=O.S(=O)(=O)(O)O.O>[CH3:1][C:2]1[C:3](=[O:22])[C:4]([C:11](=[O:21])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18](=[O:20])[CH3:19])=[C:5]([CH3:10])[C:6](=[O:9])[C:7]=1[CH3:8]

Participants

8

Reactant 4

HCID 175AcetateHCID 3283Diethyl EtherHCID 20277068HCID 20277068, compoundHCID 131709961Jones' reagent

Product 1

HCID 12906159HCID 12906159, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 2,3,5-trimethyl-6-(6'-acetoxy-1'-hydroxyhexyl)-1,4-benzoquinone (formula IV-3 wherein R=H3C, n=4, in the form of acetate at --CH2OH) (0.74 part) in acetone (20 volume parts) was oxidized at 5° C. for 5 minutes with Jones reagent (0.6 volume part) prepared by dissolving chromic trioxide (26.72 parts) in concentrated sulfuric acid (23 volume parts) diluted with water to a volume of 100 volume parts. The resulting precipitate was decomposed with water, and the product was taken up with diethyl ether. The organic layer was washed with water and dried over anhydrous sodium sulfate. The residue upon removal of the solvent was subjected to column chromatography on silica gel and eluted with methylene chloride and the resulting product was crystallized from petroleum ether to give 2,3,5-trimethyl-6-(6'-acetoxy-1'-oxohexyl)-1,4-benzoquinone (formula IV-1 wherein R=H3C, n=4, in the form of acetate) (0.638 part) as yellow crystals melting at 57° C.

Workup

  1. customprepared
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue upon removal of the solvent
  5. washeluted with methylene chloride
  6. customthe resulting product was crystallized from petroleum ether

Sources & evidence

ORD record
ord-205a2a3aa5df414e817de69878f66dc0
Source dataset
uspto-grants-1983_10
Patent number
US04407757

Reaction notes

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