Water → Nopinone

HRID 2406499Notes

Reaction equation

HRID 2406499 reaction equation
[O-][Mn](=O)(=O)=O.[K+].[OH2:7].[CH3:8][C:9]1([CH3:17])[C@H:15]2[CH2:16][C@@H:10]1[CH2:11][CH2:12][C:13]2=C>C(Cl)Cl>[CH3:8][C:9]1([CH3:17])[CH:15]2[CH2:16][CH:10]1[CH2:11][CH2:12][C:13]2=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 440967(-)-beta-PineneHCID 516875Potassium Permanganate3×

Product 1

HCID 32735Nopinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

KMnO4 (5.71 g) was ground into a fine powder and combined with acidic alumina (22.55 g) and water (5.6 mL) for 5 minutes in order to form a homogenous mixture. (−)-β-Pinene (1.16 mL), and methylene chloride (200 mL) were placed in a 250 mL roundbottom flask; the moistened KMnO4/acidic alumina was added in small portions slowly to the solution. As the KMnO4/acidic alumina was added, the reaction turned into a dark purple color solution. The reaction was allowed to continue to stir until TLC indicated all starting material had reacted. The solution was filtered through fritted glass, and the residue was washed twice with 50 mL of methylene chloride. The filtrate was concentrated and yielded 6,6-dimethyl-bicyclo[3.1.1]heptan-2-one as a light yellow oil. The oil was purified via column chromatography (85:15, Hex: EtOAc) and like fractions were combined. 1H NMR (300 MHz, CDCl3): (ppm) 0.96 (s, 3H), 1.34 (s, 3H), 1.59 (d, 1H), 1.86-2.13 (m, 2H), 2.20-2.30 (m, 1H), 2.31-2.43 (m, 1H), 2.45-2.68 (m, 3H). (ESI, Pos) m/z 161.0 (M+23).

Workup

  1. customto form a homogenous mixture
  2. customhad reacted
  3. filtrationThe solution was filtered through fritted glass
  4. washthe residue was washed twice with 50 mL of methylene chloride
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3d80d99dd17e41c9b4c416505473a15e
Source dataset
uspto-grants-2014_08
Patent number
US08809373B2

Reaction notes

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