Water → 1-[4-[(6-Bromohexyl)oxy]butyl]benzene

HRID 5209

反応式

HRID 5209 の反応式
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.O>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 76889Benzenebutanol

生成物 1

HCID 110124391-[4-[(6-Bromohexyl)oxy]butyl]benzene収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (46% dispersion in oil; 6.5 g) was added portionwise to a solution of 4-phenyl-1-butanol (15.0 g) and 1,6-dibromohexane (48.8 g) in THF (200 ml) under nitrogen. The resulting suspension was refluxed for 27 h and treated with H2O (80 ml). The mixture was extracted with ER (2×200 ml) and the dried extract was evaporated to leave an orange oil. The oil was purified on a column of silica (800 ml) [A] to give a yellow oil which on distillation gave the title compound as a colourless oil (15.0 g) b.p. 90-95/0.1 mmHg.

後処理

  1. temperatureThe resulting suspension was refluxed for 27 h
  2. extractionThe mixture was extracted with ER (2×200 ml)
  3. extractionthe dried extract
  4. customwas evaporated
  5. customto leave an orange oil
  6. customThe oil was purified on a column of silica (800 ml) [A]
  7. customto give a yellow oil which
  8. distillationon distillation

出典と根拠

ORDレコード
ord-17aed5b9702b46f69ddfc58fdccf4fd4
出典データセット
uspto-grants-1993_09
特許番号
US05243076

関連ノート

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