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

HRID 10152

反応式

HRID 10152 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a17440283c1b4d1dba9b75e78b2c71b4
出典データセット
uspto-grants-2006_08
特許番号
US07094625B2

関連ノート

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