Hydrochloric Acid → HCID 178447831、化合物

HRID 1632709

反応式

HRID 1632709 の反応式
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].Cl>O1CCCC1>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][C:13]([C:4]3[CH:9]=[CH:8][C:7]([C:13]4[CH2:14][CH2:15][CH:10]([C@H:7]5[CH2:8][CH2:9][C@H:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]5)[CH2:11][CH:12]=4)=[CH:6][CH:5]=3)=[CH:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 178447904HCID 178447904、化合物

生成物 1

HCID 178447831HCID 178447831、化合物収率 11.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of p-dibromobenzene (5.6 g, 0.024 mol) dissolved in tetrahydrofuran (200 ml) was dropwise added to sliced Mg (1.2 g, 0.049 mol) in nitrogen current so as to give soft reflux. After 7 hours, the reaction finished to yield its magnesium bromide, to which a solution of 4-(trans-4-propylcyclohexyl)-cyclohexanone (10.9 g, 0.049 mol) dissolved in tetrahydrofuran (100 ml) was rapidly dropwise added while the temperature was kept at 30° C. or lower. After the addition, the mixture was refluxed for 1.5 hour and 3N hydrochloric acid was added. The reaction liquid was extracted with toluene (100 ml×3), combined toluene layers were washed with water and the solvent was distilled off under reduced pressure. The remaining oily substance was 1,4-bis[4-(trans-4-propylcyclohexyl)-cyclohexan-1-ol]benzene, to which potassium hydrogen sulfate (2.5 g) was added, followed by dehydrating at 200° C. for 2 hours in nitrogen current, cooling, adding toluene (300 ml), filtering off potassium hydrogen sulfate, washing toluene layer with water, distilling off the solvent under reduced pressure and recrystallizing the residue from toluene to obtain an objective product, 1,4-bis[4-(trans-4-propylcyclohexyl)cyclohexen-1-yl]benzene (yield: 0.9 g) having a C-Sm point of 98.5° C. and a Sm-I point of 300° C. or higher.

後処理

  1. additionwas rapidly dropwise added while the temperature
  2. customwas kept at 30° C.
  3. additionAfter the addition
  4. temperaturethe mixture was refluxed for 1.5 hour
  5. customThe reaction liquid
  6. extractionwas extracted with toluene (100 ml×3)
  7. washwere washed with water
  8. distillationthe solvent was distilled off under reduced pressure
  9. additionto which potassium hydrogen sulfate (2.5 g) was added
  10. temperaturecooling
  11. additionadding toluene (300 ml)
  12. filtrationfiltering off potassium hydrogen sulfate
  13. washwashing toluene layer with water
  14. distillationdistilling off the solvent under reduced pressure
  15. customrecrystallizing the residue from toluene

出典と根拠

ORDレコード
ord-28eb57b589854a01a8e3413e7b8ad53f
出典データセット
uspto-grants-1984_10
特許番号
US04477369

関連ノート

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