Benzaldehyde → 2-Nitro-1-phenyl-1-propanol

HRID 1670861ノート

反応式

HRID 1670861 の反応式
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([CH2:12][CH3:13])([O-:11])=[O:10].O>O1CCCC1.C(O)(C)(C)C.CC(C)([O-])C.[K+]>[N+:9]([CH:12]([CH3:13])[CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:8])([O-:11])=[O:10]

参加物

7

反応物 3

HCID 240BenzaldehydeHCID 962WaterHCID 6587Nitroethane

生成物 1

HCID 2261182-Nitro-1-phenyl-1-propanol収率 93.7%

試薬・触媒・溶媒 3

HCID 23665647Potassium tert-butoxide触媒HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of benzaldehyde (20.0 g) and nitroethane (28.4 g) in tetrahydrofuran (50 mL) and tert-butanol (50 mL) was added potassium tert-butoxide (1.27 g) under ice-cooling, and the mixture was stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1) to give the title compound as a blue oil (yield 32.0 g, 93%).

後処理

  1. temperaturecooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=10:1)

出典と根拠

ORDレコード
ord-e249ba5e12684940b9bdf0dfb32dd26c
出典データセット
uspto-grants-2011_08
特許番号
US07994205B2

反応ノート

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