Cyclooctanone → HCID 19931302, compound

HRID 1453525Notes

Reaction equation

HRID 1453525 reaction equation
[C:1]1(=[O:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:10]([Mg]Br)[CH3:11].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:10]([C:1]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:11]

Participants

5

Reactant 3

HCID 10403CyclooctanoneHCID 516892Sodium BicarbonateHCID 178418443HCID 178418443, compound

Product 1

HCID 19931302HCID 19931302, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 1000-mL 3-necked round bottom flask equipped with a 500-mL pressure equalizing addition funnel, a nitrogen inlet with thermocouple and an overhead stirrer was added 100 g (0.79 mol) of cyclooctanone dissolved in 250 mL of dry tetrahydrofuran. The addition funnel was charged with 290 mL (0.869 mol, 10% excess) of ethyl magnesium bromide (2.0M solution in ether) which was then added to the cooled ketone over 2 hours. Stirring was continued at room temperature overnight followed by 8 hours at reflux. Excess Grignard reagent was discharged by the cautious addition of 100 mL of saturated sodium bicarbonate solution. The resulting suspension was filtered through a bed of Celite, the filtrate diluted with 500 mL of ether and the combined organics washed several times with saturated sodium bicarbonate, once with brine and then dried for 1 hr over anhydrous magnesium sulfate. Filtration and removal of the solvent at reduced pressure resulted in a light-colored oil which was distilled twice from Na2CO3 through a base-washed 15 cm Vigreux (bp 65° C.@1 mmHg) to yield 39 g (32%) of the title alcohol as a clear, colorless oil.

Workup

  1. customTo a 1000-mL 3-necked round bottom flask equipped with a 500-mL pressure
  2. additionaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
  3. waitfollowed by 8 hours
  4. temperatureat reflux
  5. filtrationThe resulting suspension was filtered through a bed of Celite
  6. additionthe filtrate diluted with 500 mL of ether
  7. dry with materialthe combined organics washed several times with saturated sodium bicarbonate, once with brine and then dried for 1 hr over anhydrous magnesium sulfate
  8. filtrationFiltration and removal of the solvent at reduced pressure
  9. customresulted in a light-colored oil which
  10. distillationwas distilled twice from Na2CO3 through a base-washed 15 cm Vigreux (bp 65° C.@1 mmHg)

Sources & evidence

ORD record
ord-3eafd6060c304d1f8d87ed590ad0bfa0
Source dataset
uspto-grants-2009_01
Patent number
US07476492B2

Reaction notes

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