Phosphorus oxychloride → 1,4-Ethanonaphthalene, 1,4-dihydro-

HRID 1879345

반응식

HRID 1879345 반응식
[CH:1]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[CH:2]2[CH:3](O)[CH:4]=[CH:5][CH:6]1O.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[CH:8]12[CH2:11][CH2:12][CH:1]([CH:10]=[CH:9]1)[C:2]1[C:7]2=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 126575751,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diol

생성물 1

HCID 1389941,4-Ethanonaphthalene, 1,4-dihydro-수율 46.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a solution of 27.9 g of tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-diol in 165 mL of pyridine were portionwise added 30 mL of POCl3 at 0° C. The reaction was stirred for 3 days at rt before it was quenched by careful addition of ice under cooling. The resulting mixture was extracted with Hept (4×50 mL). The combined organic phases were washed with H2O, 15% HCl solution and again with H2O. The organic phase was dried over MgSO4 and concentrated in vacuo to obtain 10.6 g of the desired compound as yellow oil.

후처리

  1. customat 0° C
  2. customwas quenched by careful addition of ice
  3. temperatureunder cooling
  4. extractionThe resulting mixture was extracted with Hept (4×50 mL)
  5. washThe combined organic phases were washed with H2O, 15% HCl solution and again with H2O
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4aa477d50f5c4ca08d07c8d4f8a4586d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314253B2

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