Acetone → (S)-3-Methylheptanoic acid

HRID 35724Notes

Reaction equation

HRID 35724 reaction equation
[CH3:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][CH2:4][OH:5].CC(C)=[O:12].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CO.O>[CH3:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][C:4]([OH:12])=[O:5]

Participants

7

Reactant 4

HCID 180AcetoneHCID 3776IsopropanolHCID 12490717(3S)-3-Methylheptan-1-OLHCID 131709961Jones' reagent

Product 1

HCID 10290853(S)-3-Methylheptanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 10 g. of 3-(S)-methyl-1-heptanol in 175 ml. of acetone was added over 45 minutes 90 ml. of Jones reagent dropwise at 15°-20° C. After 15 minutes, 15 ml. of isopropanol was added and stirring continued for 30 minutes. The reaction was poured into water and the product extracted with ether. The extracts were combined, washed with water, a sodium bisulfite solution and a brine solution and dried over magnesium sulfate. Removal of the solvent gave 10 g. of the product as a liquid, b.p. 84°-88° C./0.4 torr, [alpha]D =-4.46 (CH3OH C=0.105 g/ml.).

Workup

  1. customdropwise at 15°-20° C
  2. waitcontinued for 30 minutes
  3. extractionthe product extracted with ether
  4. washwashed with water
  5. dry with materiala sodium bisulfite solution and a brine solution and dried over magnesium sulfate
  6. customRemoval of the solvent
  7. customgave 10 g

Sources & evidence

ORD record
ord-4b7718dd457742439e1d252eee46b58a
Source dataset
uspto-grants-1988_08
Patent number
US04767743

Reaction notes

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