Ammonia → Cyclohexanone, trimethyl-

HRID 371964

Reaction equation

HRID 371964 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:7][CH2:6][CH2:5][CH:4](C)[C:3]1=[O:9].Cl[CH2:12]C=CCCl.N.O>C1COCC1>[CH3:12][CH:7]1[CH2:6][CH2:5][CH2:4][C:3](=[O:9])[C:2]1([CH3:1])[CH3:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 151221,4-Dichloro-2-buteneHCID 170002,2,6-Trimethylcyclohexanone

Product 1

HCID 3016570Cyclohexanone, trimethyl-Yield 19.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

28 g of 2,2,6-trimethyl-cyclohexanone are added dropwise to a suspension of Na vinylacetylide (prepared from 25 g of 1,4-dichlorobut-2-ene and 15 g of Na in liquid ammonia) in 200 ml of THF, whilst cooling, and the reaction mixture is stirred overnight at room temperature. 50 ml of water are then added, the aqueous phase is extracted with ether and the resulting organic phase is dried and concentrated. Subsequent fractional distillation gives 5.5 g of unconverted trimethylcyclohexanone and 20.7 g (corresponding to 68% of theory, based on ketone converted) of 2,2,6-trimethyl-1-(but-1'-yn-3'-en-1'-yl)-cyclohexanol of boiling point 62°-63° C/0.3 mm Hg and refractive index nD25 = 1.4982. Fragrance note: fresh, tart-woody, coniferous.

Workup

  1. temperaturewhilst cooling
  2. extractionthe aqueous phase is extracted with ether
  3. customthe resulting organic phase is dried
  4. concentrationconcentrated
  5. distillationSubsequent fractional distillation

Sources & evidence

ORD record
ord-9a4f5dd4dae64917b167c5c127b60dfe
Source dataset
uspto-grants-1978_05
Patent number
US04088681

Linked notes

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