Acetone → HCID 20485291, compound

HRID 1732670Notes

Reaction equation

HRID 1732670 reaction equation
[C:1]([C:4]([CH2:14][CH2:15][CH3:16])([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][CH2:7]CC=C)([OH:3])=[O:2].C([O-])(O)=[O:18].[Na+].[Mn]([O-])(=O)(=O)=O.[K+].OS([O-])=O.[Na+].OS(O)(=O)=O.[Mn]([O-])(=O)(=O)=O.C[C:44]([CH3:46])=[O:45]>>[C:1]([C:4]([CH2:14][CH2:15][CH3:16])([CH2:11][CH2:12][CH3:13])[CH2:5][CH2:6][CH2:7][CH2:46][C:44]([OH:18])=[O:45])([OH:3])=[O:2]

Participants

8

Reactant 7

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 24401PermanganateHCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 12850085HCID 12850085, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20485291HCID 20485291, compound

Procedure

The 7-carboxy-7-propyl-1- decene (3.42 g, 0.015 mole) prepared in Example 1A was dissolved in 75 ml of acetone, 2 g of NaHCO3 added and was cooled in an ice bath. Potassium permanganate (9.5 g, 0.06 mole) was added over four hours. The mixture was left in the cold bath for an additional hour and then NaHSO3 (8 g) was added alternately with 5 N H2SO4 to bring the pH to 2 and to reduce the residual permanganate. After filtering, the filtrate was concentrated to an oily residue which was extracted with 100 ml ethyl acetate, washed by water and saturated brine, dried (MgSO4), concentrated to give an oil weighing 3.2 g and finally distilled by molecular distillation to give the pure product.

Workup

  1. temperaturewas cooled in an ice bath
  2. waitThe mixture was left in the cold bath for an additional hour
  3. filtrationAfter filtering
  4. concentrationthe filtrate was concentrated to an oily residue which
  5. extractionwas extracted with 100 ml ethyl acetate
  6. washwashed by water and saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give an oil
  10. distillationfinally distilled by molecular distillation
  11. customto give the pure product

Sources & evidence

ORD record
ord-ba49e9c455394bc5adc119693d2e8cd3
Source dataset
uspto-grants-1980_12
Patent number
US04238389

Reaction notes

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