Anthranilic Acid → 1,4-Ethanonaphthalene, 1,4-dihydro-

HRID 10152

반응식

HRID 10152 반응식
[C:1](O)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)N.[CH:11]1[CH2:16]CC=[CH:13][CH:12]=1.N(O[CH2:20]CC(C)C)=O>O1CCCC1>[CH:2]12[CH2:8][CH2:7][CH:6]([C:5]3[C:3]1=[CH:13][CH:12]=[CH:11][CH:16]=3)[CH:20]=[CH:1]2

참가 물질

5

반응물 3

HCID 227Anthranilic AcidHCID 8053Isoamyl NitriteHCID 116051,3-Cyclohexadiene

생성물 1

HCID 1389941,4-Ethanonaphthalene, 1,4-dihydro-수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A THF solution of 1 g (7.3 mmol) of anthranilic acid was dropped into a mixed solution under reflux of 0.77 ml (8.0 mmol) of 1,3-cyclohexadiene, 1.1 ml of isoamyl nitrite and 50 ml of tetrahydrofuran. Then, the resultant solution was heated and refluxed for 2 hours to remove THF, extracted with chloroform, washed with distilled water and saturated saline, dried with anhydrous sodium sulfate and purified with silica gel column-chromatography-(chloroform) to obtain 1,4-dihydro-1,4-ethanonaphthalene (0.89 g, 5.7 mmol, yield: 78%).

후처리

  1. temperaturerefluxed for 2 hours
  2. customto remove THF
  3. extractionextracted with chloroform
  4. washwashed with distilled water and saturated saline
  5. dry with materialdried with anhydrous sodium sulfate
  6. custompurified with silica gel column-chromatography-(chloroform)

출처 및 근거

ORD 기록
ord-a17440283c1b4d1dba9b75e78b2c71b4
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094625B2

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