Allyl bromide → 1-[(Prop-1-en-1-yl)oxy]-4-[(prop-2-en-1-yl)oxy]butane

HRID 1288647ノート

反応式

HRID 1288647 の反応式
[CH:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])=[CH:2][CH3:3].[CH2:10](Br)[CH:11]=[CH2:12].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH:10]=[CH:11][CH3:12])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 543508994-[(Prop-1-en-1-yl)oxy]butan-1-ol

生成物 1

HCID 539198551-[(Prop-1-en-1-yl)oxy]-4-[(prop-2-en-1-yl)oxy]butane収率 75%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

実験手順

A mixture of 20 g 4(1-propenoxy)-1-butanol (0.15 moles), 24.2 g allyl bromide (0.2 moles), 1.26 g tetra-n-butylammonium bromide (3.9 mmoles); 8 g sodium hydroxide (0.2 moles); and 60 mL toluene were stirred at 60° C. for ten hours. After cooling, the reaction mixture was filtered to remove inorganic salts and the filtrate was poured into distilled water. The organic layer was separated and the aqueous layer was washed again with fresh toluene. The toluene layers were combined and the solvent removed on a rotary evaporator leaving 1-allyloxy-4(1-propenoxy)butane (an α-allyloxy-ω-(1-propenoxy)alkane) as a clear oil. Further purification was accomplished by distillation at 110° C. under a vacuum of 0.7 mm Hg, obtaining a 75% yield.

後処理

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customto remove inorganic salts
  4. additionthe filtrate was poured
  5. distillationinto distilled water
  6. customThe organic layer was separated
  7. washthe aqueous layer was washed again with fresh toluene
  8. customthe solvent removed on a rotary evaporator

出典と根拠

ORDレコード
ord-343ebebd0b604f3faad4a4fee20173aa
出典データセット
uspto-grants-1998_05
特許番号
US05747172

反応ノート

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