Sodium Carbonate → HCID 70396540, compound

HRID 1789563Notes

Reaction equation

HRID 1789563 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2.C(=O)([O-])[O-:17].[Na+].[Na+].[Mn]([O-])(=O)(=O)=O.[K+]>>[C:2]([CH2:3][CH2:4][CH2:5][CH:6]=[C:7]1[CH2:14][CH2:13][CH:12]2[CH:8]1[CH2:9][C:10](=[O:15])[CH2:11]2)([OH:17])=[O:1]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 516875Potassium PermanganateHCID 14204106HCID 14204106, compound

Product 1

HCID 70396540HCID 70396540, compound

Procedure

2-(5-Hydroxypent-1-yl)bicyclo[3.3.0]octan-7-one {hexahydro-4-(5-hydroxyheptyl)-2(1H)-pentalenone} (0.5 g, 2.4 mmoles) is mixed with a 10% solution of sodium carbonate (0.51 ml). The reaction is cooled in an ice bath and solution of potassium permanganate (0.48 g dissolved in 12 ml water) is slowly added over 10 minutes. The ice bath is then removed and the reaction mixture stirred at room temperature for 12 hour, after which time the precipitated manganese dioxide is filtered off and the filtrate partitioned between ether. The solution is acidified with dilute sulfuric acid and the organic layer separated. The aqueous phase is extracted with ether (2×20 ml), and the ether extracts combined and dried over anhydrous sodium sulfate. The solvent is removed under vacuum leaving a clear colorless oil. The crude product is chromatographed on silica gel and subsequently kugelrohred under reduced pressure leaving a clear, colorless oil (0.050 g, 0.22 mmoles).

Workup

  1. temperatureThe reaction is cooled in an ice bath
  2. customThe ice bath is then removed
  3. filtrationafter which time the precipitated manganese dioxide is filtered off
  4. customthe filtrate partitioned between ether
  5. customthe organic layer separated
  6. extractionThe aqueous phase is extracted with ether (2×20 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is removed under vacuum
  9. customleaving a clear colorless oil
  10. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-aaa9d570889e44ab9e15ae39b0318a51
Source dataset
uspto-grants-1987_08
Patent number
US04689345

Reaction notes

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