Hydrochloric Acid → HCID 178447831, 화합물

HRID 1632709

반응식

HRID 1632709 반응식
[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]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 178447904HCID 178447904, 화합물

생성물 1

HCID 178447831HCID 178447831, 화합물수율 11.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-28eb57b589854a01a8e3413e7b8ad53f
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04477369

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