Cyclohexanone → 1-Oxaspiro[5.5]undec-3-ene, 4-methyl-

HRID 716487노트

반응식

HRID 716487 반응식
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][C:9]([CH2:11][CH2:12]O)=[CH2:10]>CC1C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>[CH3:8][C:9]1[CH2:10][C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[O:7][CH2:12][CH:11]=1

참가 물질

5

반응물 2

HCID 7967CyclohexanoneHCID 129883-Methyl-3-buten-1-ol

생성물 1

HCID 111164241-Oxaspiro[5.5]undec-3-ene, 4-methyl-수율 80%

시약·촉매·용매 2

HCID 6101p-Toluenesulfonic acid촉매HCID 1140Toluene용매

반응 조건

온도
115 °C

실험 절차

A mixture of p-TSA (20 g, 0.105 mol) and toluene (2 L) was heated to 115° C. To this mixture were added cyclohexanone (980 g, 10 mols) and isoprenol (946 g, 11 mols) and heated further for 3-6 h. Water was removed from the reaction azeotropically. The reaction mixture was then cooled to room temperature. The organic phase was washed with a 5% Na2CO3 solution, washed with water dried and concentrated and distilled further to provide 4-methyl-1-oxaspiro [5.5] undec-3-ene (1.32 kg) having a purity of 98% (sum of the isomers) for a total yield of 80%.

후처리

  1. temperatureheated further for 3-6 h
  2. customWater was removed from the reaction azeotropically
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. washThe organic phase was washed with a 5% Na2CO3 solution
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. distillationdistilled further

출처 및 근거

ORD 기록
ord-164427831c5d4e9e8728c6430438f806
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187709B2

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