Hydrochloric Acid → HCID 13782562, compound

HRID 1249327Notes

Reaction equation

HRID 1249327 reaction equation
[Mg].[CH2:2](Br)[CH:3]=[CH2:4].[CH3:6][C:7]1([CH3:16])[CH2:12][CH2:11][CH2:10][C:9]([CH3:14])([CH3:13])[C:8]1=[O:15].Cl>O.C(OCC)C>[CH2:4]([C:8]1([OH:15])[C:9]([CH3:14])([CH3:13])[CH2:10][CH2:11][CH2:12][C:7]1([CH3:16])[CH3:6])[CH:3]=[CH2:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 1369332,2,6,6,-TetramethylcyclohexanoneHCID 5462224Magnesium

Product 1

HCID 13782562HCID 13782562, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium (11.5 g, 0.48 moles) and dried diethyl ether (300 ml) were added, in this order, to one liter four-necked flask equipped with a mechanical stirrer, a dropping funnel, a thermometer, a reflux condenser and a nitrogen gas inlet tube and stirred at room temperature. While stirring at room temperature, a mixed solution of allyl bromide (57.7 g, 0.48 moles)/dried diethyl ether (100 ml) was dropped to the mixture in 2 hours. The resulting mixture was heated under reflux for 30 minutes. Into the mixture was dropped a mixed solution of 2,2,6,6-tetramethylcyclohexanone (49 g, 0.32 moles)/dried diethyl ether (100 ml) in about 40 minutes while stirring under heating and refluxing conditions. The mixture was further stirred for 2 hours under refluxing conditions. The resultant reaction mixture was poured into iced water, followed by adding a 1N hydrochloric acid aqueous solution to render the mixture weakly acidic and separating it into two layers. The organic layer was washed with a saturated sodium bicarbonate aqueous solution (50 ml) and then with water (50 ml) three times. The organic layer was dried over anhydrous magnesium sulfate and separated by filtration, followed by concentration and fractionation to obtain 42.7 g (yield 68%) of the captioned compound. This compound was a colorless transparent liquid having a woody, green, earthy and patchuli oil-like odor.

Workup

  1. customequipped with a mechanical stirrer, a dropping funnel
  2. stirringWhile stirring at room temperature
  3. temperatureThe resulting mixture was heated
  4. temperatureunder reflux for 30 minutes
  5. stirringwhile stirring
  6. temperatureunder heating
  7. temperaturerefluxing conditions
  8. stirringThe mixture was further stirred for 2 hours under refluxing conditions
  9. customThe resultant reaction mixture
  10. customseparating it into two layers
  11. washThe organic layer was washed with a saturated sodium bicarbonate aqueous solution (50 ml)
  12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  13. customseparated by filtration
  14. concentrationfollowed by concentration and fractionation

Sources & evidence

ORD record
ord-87df1059518144188a6165f26cde1380
Source dataset
uspto-grants-1986_12
Patent number
US04631147

Reaction notes

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