Triethylene Glycol → 4-(4-Methylpentyl)bromobenzene

HRID 257985

반응식

HRID 257985 반응식
[OH-].[K+].C(O)COCCOCCO.O=[C:14]([C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=1)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18].O.NN>>[CH3:18][CH:17]([CH3:19])[CH2:16][CH2:15][CH2:14][C:20]1[CH:21]=[CH:22][C:23]([Br:26])=[CH:24][CH:25]=1

참가 물질

5

반응물 4

HCID 8172Triethylene GlycolHCID 14797Potassium Hydroxide2회HCID 24654Hydrazine hydrate (1:1)HCID 224090794-(1-Oxo-4-methyl-pentyl) bromobenzene2회

생성물 1

HCID 224090934-(4-Methylpentyl)bromobenzene

반응 조건

온도
100 °C

실험 절차

A mixture of 6.45 g (115 mmol) of potassium hydroxide and 42 ml of triethylene glycol was heated at around 100 degrees C. until the potassium hydroxide was dissolved. The mixture was allowed to cool and then treated with 10 g (39mmol) of 4-(1-oxo-4-methylpentyl) bromobenzene (Compound 29) followed by 3 g (94 mmol) of hydrazine hydrate. The mixture was slowly brought to reflux and heated at reflux for 1 hour. The apparatus was modified for distillation and the mixture heated until approximately 7 ml of liquid had distilled over and the flask temperature had reached 220 degrees C. The apparatus was again modified for reflux and the mixture was heated at reflux for 5 hours and then stirred at room temperature for 8.5 hours. The mixture was then heated to 100 degrees C. and poured into 40 ml of water and the flask rinsed with an additional 25 ml of water. This diluted mixture was acidified to pH=2 with conc. HCl and extracted with ether. The ether extract was washed successively with water and saturated NaCl and then dried (MGSO4). The solvent was removed in vacuo and the residue subjected to kugelrohr distillation (70 degrees C., 0.05 mm) to give the title compound as a colorless oil. PMR (CDCl3) : & 0.88 (6H, d, J~6 Hz), 1.12-1.26 (2H, m), 1.48-1.66 (3H, m), 2.54 (2H, t, J~7.7 Hz) 7.06 (2H, d, J~8.3 Hz), 7.39 (2H, d, J~8.3 Hz).

후처리

  1. temperatureto cool
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureat reflux for 1 hour
  5. distillationThe apparatus was modified for distillation
  6. temperaturethe mixture heated until approximately 7 ml of liquid
  7. distillationhad distilled over and the flask temperature
  8. customhad reached 220 degrees C
  9. temperaturefor reflux
  10. temperaturethe mixture was heated
  11. temperatureat reflux for 5 hours
  12. temperatureThe mixture was then heated to 100 degrees C
  13. additionand poured into 40 ml of water
  14. washthe flask rinsed with an additional 25 ml of water
  15. extractionextracted with ether
  16. extractionThe ether extract
  17. washwas washed successively with water and saturated NaCl
  18. customdried (MGSO4)
  19. customThe solvent was removed in vacuo
  20. distillationthe residue subjected to kugelrohr distillation (70 degrees C., 0.05 mm)

출처 및 근거

ORD 기록
ord-3fba70fbad5d4358873c97fa36844ec4
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264456

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