1-Bromohexane → 2,6-Dibromo-1,5-bis(hexyloxy)naphthalene

HRID 645306ノート

反応式

HRID 645306 の反応式
[O-][CH2:2][CH3:3].[Na+].[Br:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:17])[C:12]=2[OH:16])[C:7]=1[OH:18].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[Br:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:17])[C:12]=2[O:16][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:7]=1[O:18][CH2:15][CH2:6][CH2:7][CH2:8][CH2:2][CH3:3]

参加物

5

反応物 3

HCID 81011-BromohexaneHCID 962602,6-Dibromo-1,5-naphthalenediolHCID 2723922Sodium ethoxide

生成物 1

HCID 183321032,6-Dibromo-1,5-bis(hexyloxy)naphthalene収率 48%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Under an inert atmosphere, sodium ethoxide (2.76 g, 40.6 mmol) and 2,6-dibromo-1,5-di hydroxynaphthalene (5 g, 15.7 mmol) were dissolved in ethanol (60 ml). Under reflux, ethanol solution (10 ml) of hexylbromide (6.7 g, 40.6 mmol) was added dropwise in 10 minutes. It was refluxed for 5 hours and then left for cooling. The reaction mixture was added to 1N sodium-hydroxide aqueous solution, and the depositing precipitate was filtrated. The precipitate was washed with methylene chloride, and the washed solution was concentrated under a reduced pressure to obtain a crude product. The desired product was obtained after purifying by silica gel chromatography (toluene:hexane=4:1).

後処理

  1. temperatureUnder reflux
  2. temperatureIt was refluxed for 5 hours
  3. waitleft
  4. temperaturefor cooling
  5. additionThe reaction mixture was added to 1N sodium-hydroxide aqueous solution
  6. filtrationthe depositing precipitate was filtrated
  7. washThe precipitate was washed with methylene chloride
  8. concentrationthe washed solution was concentrated under a reduced pressure
  9. customto obtain a crude product

出典と根拠

ORDレコード
ord-1fec327efe3a452790a109fd95f209c2
出典データセット
uspto-grants-2010_04
特許番号
US07701129B2

反応ノート

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