Hydrochloric Acid → HCID 22861697, compound

HRID 259873Notes

Reaction equation

HRID 259873 reaction equation
[CH3:1][C@@H:2]([CH2:5][CH2:6][CH:7]=C(C)C)[CH:3]=[CH2:4].[Mn]([O-])(=O)(=O)=O.[K+].I([O-])(=O)(=O)=O.[Na+].[C:23](=[O:26])([O-])[O-:24].[K+].[K+].[OH-:29].[Na+].Cl.N([O-])=[O:33].[Na+]>O.C(O)(C)(C)C>[CH3:1][C@@H:2]([CH2:5][CH2:6][CH3:7])[CH:3]([C:23]([OH:24])=[O:26])[C:4]([OH:33])=[O:29]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 10887985(S)-CitronelleneHCID 23667635Sodium periodateHCID 23668193Sodium Nitrite

Product 1

HCID 22861697HCID 22861697, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

(S)-3,7-Dimethyl-1,6-octadiene (85% ee) (61 mg, 0.44 mmol) was dissolved in a mixture of water (20 ml) and tert.-butanol (10 ml). To the solution cooled with ice, potassium permanganate, (185 mg, 1.17 mmol), sodium metaperiodate (1.46 g, 6.86 mmol) and potassium carbonate (366 mg, 2.64 mmol) were added. To the reaction mixture, a 3N aqueous solution of sodium hydroxide was added to adjust pH to 8, followed by stirring at room temperature for 2 hours. While cooling with ice, conc. hydrochloric acid was added to the reaction mixture to adjust pH to 1. Then, sodium nitrite was added till the color of solution was changed from reddish brown to yellow, and the reaction mixture was extracted with diethyl ether. The organic layer was extracted with a 3N aqueous solution of sodium hydroxide twice, and thereafter, the aqueous layer was washed with diethyl ether once. To the aqueous layer, conc. hydrochloric acid was added to adjust pH to 1, and then the aqueous layer was extracted with diethyl ether three times. After drying the organic layer over anhydrous magnesium sulfate, the solvent was evaporated off under reduced pressure to obtain (S)-2-methylpentane dicarboxylic acid as a pale yellow oil (38 mg). Yield, 58%. Optical purity, 85% ee. Rotatory power: :[α]D20 =+17.4 (C=1.63, CHCl3). 1H-NMR (CDCl3): δ(ppm)=1.23 (d, J=7.0 Hz, 3H), 1.8-2.1 (m, 2H), 2.4-2.7 (m, 3H), 9.0-10.5 (br, 2H).

Workup

  1. additionwere added
  2. additionwas added to the reaction mixture
  3. extractionwas extracted with diethyl ether
  4. extractionThe organic layer was extracted with a 3N aqueous solution of sodium hydroxide twice
  5. washthe aqueous layer was washed with diethyl ether once
  6. additionTo the aqueous layer, conc. hydrochloric acid was added
  7. extractionthe aqueous layer was extracted with diethyl ether three times
  8. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  9. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-a3620ba67dcd42c0a9133dcef72a79dc
Source dataset
uspto-grants-1996_06
Patent number
US05523437

Reaction notes

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