Triethylene glycol divinyl ether → 4-Methyl-3-(4-methylphenyl)-4-pentenal

HRID 2387592

반응식

HRID 2387592 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]([CH3:11])=[CH2:10])=[CH:4][CH:3]=1.[CH2:13]=[CH:14][O:15]CCOCCOCCOC=C>C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH3:11][C:9](=[CH2:10])[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:13][CH:14]=[O:15]

참가 물질

4

반응물 2

HCID 3033992Triethylene glycol divinyl etherHCID 540233242-Methyl-1-(4-methylphenyl)prop-2-en-1-ol

생성물 1

HCID 873705594-Methyl-3-(4-methylphenyl)-4-pentenal수율 45.4%

시약·촉매·용매 1

HCID 15337Mercuric acetate촉매

실험 절차

(3E)-(4-Methylphenyl)-2-methyl-2-propen-1-ol (17.33 g, 0.102 mol), tri (ethylene glycol) divinyl ether (Aldrich 98%, 20.5 g, 0.102 mol) and mercury(II) acetate (1 g, 0.003 mol) were heated together under nitrogen at 155-160° C. (bath temperature) for 3 hours. After cooling to room temperature, the reaction was diluted with heptanes, washed with water (3 times). Each aqueous phase was re-extracted with heptanes. Combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with heptanes and the solvent was removed under vacuum. The crude product was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate (11:1) followed by bulb-to-bulb distillation (81° C./0.002 mbar). 8.71 g of the desired product were obtained (yield=43%).

후처리

  1. washwashed with water (3 times)
  2. extractionEach aqueous phase was re-extracted with heptanes
  3. dry with materialCombined extracts were dried over solid anhydrous sodium sulfate
  4. filtrationThe solid was filtered off
  5. washrinsed with heptanes
  6. customthe solvent was removed under vacuum
  7. customThe crude product was purified by column chromatography on silica gel (eluent
  8. distillationheptanes/ethyl acetate (11:1) followed by bulb-to-bulb distillation (81° C./0.002 mbar)

출처 및 근거

ORD 기록
ord-9151c505dcbf4730b0a2e6c2ab9135d9
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268895B2

연결된 노트

불러오는 중…