Ammonia → Cyclohexanone, trimethyl-

HRID 371964

반응식

HRID 371964 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 3016570Cyclohexanone, trimethyl-수율 19.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9a4f5dd4dae64917b167c5c127b60dfe
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04088681

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