Bromoethene → 1,4-Pentadien-3-ol, 3-methyl-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-

HRID 567390

반응식

HRID 567390 반응식
[Mg].[CH:2](Br)=[CH2:3].[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:7]=1/[CH:14]=[CH:15]/[C:16]([CH3:18])=[O:17]>C1COCC1>[CH3:5][C:6]1[CH2:11][CH2:10][CH2:9][C:8]([CH3:12])([CH3:13])[C:7]=1/[CH:14]=[CH:15]/[C:16]([OH:17])([CH:2]=[CH2:3])[CH3:18]

참가 물질

5

반응물 3

HCID 11641Bromoethene2회HCID 638014I2-IononeHCID 5462224Magnesium

생성물 1

HCID 64368461,4-Pentadien-3-ol, 3-methyl-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-수율 837.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
7.5 °C

실험 절차

0.1 mols of magnesium turnings are suspended in 50 ml of THF and treated with some drops of a solution of 0.12 mols of vinyl bromide in 100 ml of THF with stirring and under nitrogen atmosphere. As soon as the Grignard starts to form, the mixture is is cooled to 5-10° C. and added with the remaining solution of vinyl bromide in 30 min. The mixture is then cooled to −60° C. and added with 0.09 mols of beta ionone in 100 ml of THF in 20 min. The mixture is left to warm to room temperature, then heated at 40° C. for 2 hours. After that, the reaction is quenched as above described and vinyl beta-ionol is recovered by double distillation under vacuum, to obtain 166 g of a product, corresponding to an about 84% yield, with purity higher than 90%, determined by NMR.

후처리

  1. customto form
  2. temperatureThe mixture is then cooled to −60° C.
  3. waitThe mixture is left
  4. temperatureto warm to room temperature
  5. temperatureheated at 40° C. for 2 hours
  6. customAfter that, the reaction is quenched as
  7. distillationvinyl beta-ionol is recovered by double distillation under vacuum

출처 및 근거

ORD 기록
ord-209895f0c3fa4b99a666bb710cc5c737
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177579B1

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