18-Crown-6 → 3-(1,3-Dioxolan-2-YL)benzophenone

HRID 1666781Notes

Reaction equation

HRID 1666781 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([CH:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[OH:13])[CH:9]=[CH:10][CH:11]=1.C1OCCOCCOCCOCCOCCOC1.[Mn]([O-])(=O)(=O)=O.[K+].S([O-])(O)=O.[Na+]>ClCCl.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[C:8]([C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 516875Potassium PermanganateHCID 10824966(3-[1,3]Dioxolan-2-ylphenyl)phenylmethanolHCID 23665763Sodium Bisulfite

Product 1

HCID 105150883-(1,3-Dioxolan-2-YL)benzophenone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Combine (3-[1,3]dioxolan-2-ylphenyl)phenyl-methanol (5.0 g, 18.5 mmol) and 18-crown-6 (160 mg, 0.6 mmol) in dichloromethane. Add potassium permanganate (8.8 g, 55.5 mmol). Heat to about 40° C. After 4 hours, cool to room temperature add water and sodium hydrogensulfite (6.0 g). Basify with a solution of 1N sodium hydroxide (about 60 ml) and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with EtOAc to give the title compound.

Workup

  1. temperaturecool to room temperature
  2. extractionBasify with a solution of 1N sodium hydroxide (about 60 ml) and extract with dichloromethane
  3. washwash sequentially with distilled water and brine
  4. dry with materialdry (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customto give a residue
  8. washChromatograph the residue eluting with EtOAc

Sources & evidence

ORD record
ord-0d86c8fd5083483ba9145f72cc22cecb
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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