Water → 1-Ethynylcyclohexene

HRID 371962

반응식

HRID 371962 반응식
[C:1]([C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1)#[CH:2].[H-].[Na+].[CH3:11][CH:12]1[CH:17]([CH3:18])[CH2:16][CH2:15][CH:14]([CH3:19])[C:13]1=[O:20].O>O1CCCC1.CCOCC>[C:1]([C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1)#[CH:2].[CH3:11][CH:12]1[CH:17]([CH3:18])[CH2:16][CH2:15][CH:14]([CH3:19])[C:13]1([C:2]#[C:1][C:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]=1)[OH:20]

참가 물질

8

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 791281-EthynylcyclohexeneHCID 1425832,3,6-Trimethylcyclohexan-1-one

생성물 2

HCID 791281-EthynylcyclohexeneHCID 203524611-(2,3,6-Trimethyl-1-hydroxy-cyclohexyl)-2-(cyclohex-1-en-1-yl)-acetylene

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

21.5 g of ethynylcyclohexene are added dropwise to a suspension of 6 g of 80% strength sodium hydride in 200 ml of tetrahydrofuran under reflux, and the reaction mixture is kept under reflux conditions until no further gas is evolved. 28 g of 2,3,6-trimethyl-cyclohexanone are then added dropwise at room temperature and the mixture is left overnight, whilst being stirred, in order to complete the reaction. Water is added to the reaction mixture, the reaction product is taken up in ether and the ether solution is washed with water, dried and concentrated. Fractional distillation gives 9 g of unconverted ethynylcyclohexene, 8 g of starting ketone, and 22 g of 1-(2,3,6-trimethyl-1-hydroxy-cyclohexyl)-2-(cyclohex-1-en-1-yl)-acetylene of boiling point 120° C/0.1 mm Hg and refractive index nD25 = 1.5143. This corresponds to a yield of 68% of theory, based on trimethylcyclohexanone converted. Fragrance note: faint, tart, herbaceous.

후처리

  1. temperatureunder reflux
  2. customthe reaction
  3. washthe ether solution is washed with water
  4. customdried
  5. concentrationconcentrated
  6. distillationFractional distillation

출처 및 근거

ORD 기록
ord-c49b3e6afff64eb6bb4958e2c9f6e8a1
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04088681

연결된 노트

불러오는 중…