Sodium Methoxide → HCID 56998058, compound

HRID 1608074Notes

Reaction equation

HRID 1608074 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:7]=[C:6]([CH3:8])[CH2:5][C:4]([CH3:10])([CH3:9])[CH:3]1[C:11](=[CH2:16])[CH2:12][C:13](=[O:15])[CH3:14].C[O-].[Na+]>CO>[CH3:1][C:2]1([CH3:17])[CH:7]=[C:6]([CH3:8])[CH2:5][C:4]([CH3:9])([CH3:10])[CH:3]1[C:11]([CH3:16])=[CH:12][C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14692980HCID 14692980, compound

Product 1

HCID 56998058HCID 56998058, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(2,2,4,6,6,-pentamethyl-3-cyclohexen-1-yl)-4-penten-2-one (1.50 g, 0.0063 mol) methanol (30 mL) and sodium methoxide (0.02 g) was stirred at 25° C. for 18 hr. The mixture was then heated at reflux for 3 hr. The mixture was cooled to 25° C. and most of the methanol was evaporated under reduced pressure. The residue was partitioned between ether (75 mL) and water (15 mL). The aqueous layer was extracted with ether (50 mL). The ether extracts were washed with saturated sodium bicarbonate solution, brine and dried. Evaporation of solvents and kugelrohr distillation of the residue provided 1.28 g (85% yield) of 4-(2,2,4,6,6-pentamethyl-3-cyclohexen-1-yl)-3-penten-2-one (GLC purity: 93.5%). 1H-NMR (60 MHz) δ0.93 (12h, broad s), 1.57 (3H, broad s), 1.5-1.9 (2H, m), 1.88 (1H, broad s), 3.42 (3H, s), 5.01 (1H, broad s), 6.02 (1H, broad s); IR (film) vmax 2950, 1685, 1600, 1440, 1380, 1365 cm-1 ; MS m/e 234, 216, 191, 149, 135, 121.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 3 hr
  3. customwas evaporated under reduced pressure
  4. customThe residue was partitioned between ether (75 mL) and water (15 mL)
  5. extractionThe aqueous layer was extracted with ether (50 mL)
  6. washThe ether extracts were washed with saturated sodium bicarbonate solution, brine
  7. customdried
  8. customEvaporation of solvents and kugelrohr distillation of the residue

Sources & evidence

ORD record
ord-03d23470c5a0449aa7839a301eacc58c
Source dataset
uspto-grants-1989_09
Patent number
US04868339

Reaction notes

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