Chromic Acid → 4,4-Diphenylnon-8-en-3-one

HRID 1461149Notes

Reaction equation

HRID 1461149 reaction equation
[C:1]1([C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[CH:8]([OH:11])[CH2:9][CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](O)(O)(=O)=O>CC(C)=O>[C:17]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])[C:8](=[O:11])[CH2:9][CH3:10])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 24425Chromic AcidHCID 199815114,4-Diphenylnon-8-en-3-ol

Product 1

HCID 199815084,4-Diphenylnon-8-en-3-oneYield 78.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

One hundred seventy milligrams of 4,4-diphenylnon-8-en-3-ol was dissolved in acetone (10 ml), and then treated with 2.7M chromic acid solution (0.04 ml). After 10 min, the excess oxidant was destroyed with isopropanol, and the mixture was diluted with ether (20 ml). Filtration through a pad of celite and concentration yielded 133 mg of 4,4-diphenylnon-8-en-3-one, as an amorphous white solid.

Workup

  1. customthe excess oxidant was destroyed with isopropanol
  2. additionthe mixture was diluted with ether (20 ml)
  3. filtrationFiltration
  4. concentrationthrough a pad of celite and concentration

Sources & evidence

ORD record
ord-ed73cb74f4f64592b7d42a4b31c17767
Source dataset
uspto-grants-1991_12
Patent number
US05073629

Reaction notes

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