Methanol → 2-Methoxy-5,5-dimethylcyclohex-2-enone

HRID 44585Notes

Reaction equation

HRID 44585 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][CH:7]2[CH:5]([O:6]2)[C:4](=[O:9])[CH2:3]1.[OH-].[K+].[CH3:13]O>O>[CH3:13][O:6][C:5]1[C:4](=[O:9])[CH2:3][C:2]([CH3:10])([CH3:1])[CH2:8][CH:7]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 14797Potassium HydroxideHCID 135530454,4-Dimethyl-7-oxabicyclo[4.1.0]heptan-2-one

Product 1

HCID 552979862-Methoxy-5,5-dimethylcyclohex-2-enoneYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4,4-dimethyl-7-oxa-bicyclo[4.1.0]heptan-2-one (44.0 g, 0.31 mol) in methanol (150 mL) was added to a solution of 85% potassium hydroxide (20.7 g, 0.31 mol) in methanol (450 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 (1.2 L) and extracted with ethyl ether (350 mL×5). The organic extracts were collected, washed with brine, dried on Na2SO4 and evaporated under vacuum to remove most of the solvent. The crude material was purified by distillation to obtain pure the title compound (32.8 g, 68% yield) as an oil.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. extractionextracted with ethyl ether (350 mL×5)
  5. customThe organic extracts were collected
  6. washwashed with brine
  7. customdried on Na2SO4
  8. customevaporated under vacuum
  9. customto remove most of the solvent
  10. distillationThe crude material was purified by distillation

Sources & evidence

ORD record
ord-569f640ad5bc4509979fa057eae927af
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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