Methanol → HCID 586875, compound

HRID 875097Notes

Reaction equation

HRID 875097 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:8]2[CH:6]([O:7]2)[C:5](=[O:9])[CH2:4][CH2:3]1.[OH-].[K+].[CH3:13]O>O>[CH3:13][O:7][C:6]1[C:5](=[O:9])[CH2:4][CH2:3][C:2]([CH3:10])([CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14797Potassium HydroxideHCID 122946565,5-Dimethyl-7-oxabicyclo[4.1.0]heptan-2-one

Product 1

HCID 586875HCID 586875, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5,5-dimethyl-7-oxabicyclo[4.1.0]heptan-2-one (19.4 g, 138.4 mmol) in methanol (95 mL) was added to a solution of 85% potassium hydroxide (9.1 g, 138.4 mmol) in methanol (285 mL) at room temperature. The mixture was kept at this temperature for 20 hours and was then heated to reflux for 30 minutes. After cooling, the solution was diluted with water (750 mL) and extracted with diethyl ether (350 mL×4). The organic extracts were collected, washed with brine, dried on Na2SO4 and evaporated to dryness. The crude material was taken up with hexane (380 mL), maintained under vigorous stirring for 30 minutes and filtered to remove the solid material. The filtrate was evaporated under vacuum to obtain the pure title compound (9.8 g, 45.9% yield) as a pale yellow oil.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. extractionextracted with diethyl ether (350 mL×4)
  5. customThe organic extracts were collected
  6. washwashed with brine
  7. customdried on Na2SO4
  8. customevaporated to dryness
  9. temperaturemaintained
  10. filtrationfiltered
  11. customto remove the solid material
  12. customThe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-d833f82853f941ea91294169a6101f4b
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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