Toluene → 5-Isopropyl-1,3-dimethyl-bicyclo[3.2.1]oct-3-en-2-one

HRID 638791노트

반응식

HRID 638791 반응식
[CH3:1][C:2]1[C:3](=[O:14])[C:4]([CH3:13])([CH2:8][CH:9]=C(C)C)[CH2:5][CH2:6][CH:7]=1.C([Al](Cl)Cl)C.[NH4+].[Cl-].[C:22]1(C)[CH:27]=CC=C[CH:23]=1>>[CH:22]([C:6]12[CH2:5][C:4]([CH3:13])([CH2:8][CH2:9]1)[C:3](=[O:14])[C:2]([CH3:1])=[CH:7]2)([CH3:27])[CH3:23]

참가 물질

5

반응물 4

HCID 1140TolueneHCID 11237Ethylaluminum dichlorideHCID 25517Ammonium ChlorideHCID 115792582,6-Dimethyl-6-(3-methyl-but-2-enyl)-cyclo-hex-2-enone

생성물 1

HCID 450987025-Isopropyl-1,3-dimethyl-bicyclo[3.2.1]oct-3-en-2-one수율 90%

실험 절차

To a solution of 2,6-dimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enone (5.00 g, 26.04 mmol) in toluene (40 ml) was added dropwise neat EtAlCl2 (97%, 1.5 eq., 4.96 g, 39.06 mmol). During the addition, the temperature was kept below 10° C. The brown mixture was kept at room temperature over night and was then poured on icecold saturated NH4Cl. The mixture was extracted with MTBE, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled bulb to bulb to yield 4.50 g (90%) of an colorless oil.

후처리

  1. additionDuring the addition
  2. customwas kept below 10° C
  3. waitThe brown mixture was kept at room temperature over night
  4. extractionThe mixture was extracted with MTBE
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. distillationThe residue was distilled bulb to bulb

출처 및 근거

ORD 기록
ord-46c8f7c24d3c44b4b8e49d55ad04b40d
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691802B2

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