1,4-Dioxane → Citronellol

HRID 1973205ノート

反応式

HRID 1973205 の反応式
C([O:4][CH2:5][CH2:6][C:7]([CH3:15])=[CH:8][CH2:9][CH2:10][C:11](Cl)([CH3:13])[CH3:12])(=O)C.O1CCOCC1.[H][H]>O.[Pd]>[CH3:12][C:11](=[CH:10][CH2:9][CH2:8][CH:7]([CH2:6][CH2:5][OH:4])[CH3:15])[CH3:13]

参加物

6

反応物 3

HCID 312751,4-DioxaneHCID 537651067-Chloro-3,7-dimethyl-3-octenyl acetateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 8842Citronellol収率 70%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

実験手順

1 mole of 7-chloro-3,7-dimethyl-3-octenyl acetate was dissolved into 200 milliliters of dioxane and the solution was subjected to hydrogenation reaction in a reactor containing 20 grams of activated palladium black at about 25° C. under normal pressure until hydrogen was no more absorbed. Then, palladium black was filtered off, from the reaction mixture and dioxane was distilled off from the filtrate under reduced pressure. The residual liquid was added to the solution of 40 grams of sodium hydroxide in 200 milliliters of methanol, and heated under reflux for 72 hours. The resulting reaction mixture was diluted with 1200 milliliters of water, and the oil layer was separated from the aqueous layer. The oil layer thus separated was washed with 200 milliliters of water three times and then dried over 20 grams of Glauber's salt (sodium sulfate). By distillation of the oil layer under reduced pressure a fraction having a boiling point range of 110°-118° C./15mmHg was collected, whereby 0.7 mole of citronellol was obtained.

後処理

  1. customthe solution was subjected to hydrogenation reaction in a reactor
  2. customno more absorbed
  3. filtrationThen, palladium black was filtered off, from the reaction mixture and dioxane
  4. distillationwas distilled off from the filtrate under reduced pressure
  5. additionThe residual liquid was added to the solution of 40 grams of sodium hydroxide in 200 milliliters of methanol
  6. temperatureheated
  7. temperatureunder reflux for 72 hours
  8. customThe resulting reaction mixture
  9. customthe oil layer was separated from the aqueous layer
  10. customThe oil layer thus separated
  11. washwas washed with 200 milliliters of water three times
  12. dry with materialdried over 20 grams of Glauber's salt (sodium sulfate)
  13. distillationBy distillation of the oil layer under reduced pressure a fraction
  14. customa boiling point range of 110°-118° C./15mmHg
  15. customwas collected

出典と根拠

ORDレコード
ord-ffb2bda670034c569e4eeac8fecd2622
出典データセット
uspto-grants-1976_12
特許番号
US03996303

反応ノート

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