4-Nitrophenol → 6-(4-Nitrophenoxy)-hexanoic acid methyl ester

HRID 501842

反応式

HRID 501842 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>CC(C)=O>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 9804-NitrophenolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 4170292Methyl 6-Bromohexanoate

生成物 1

HCID 146502956-(4-Nitrophenoxy)-hexanoic acid methyl ester収率 65.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a mixture of 4-nitrophenol (150 g, 1.079 moles), potassium carbonate (600 g, 4.341 moles) and sodium iodide (10 g, 66.7 mmol) in anhydrous acetone (2.1 L) was added methyl 6-bromohexanoate (156 g, 746.41 mmol) with and heating to reflux for 48 hours. Acetone was distilled off and water (2 L) was added. Crude 21 was filtered, dried and recrystallised from a mixture of ethyl acetate:hexane (1:6) to get pure 21 (130 g, 45.1%) as a white powder with an m.p. between 84.5.5-86.6° C.

後処理

  1. temperatureheating
  2. temperatureto reflux for 48 hours
  3. distillationAcetone was distilled off
  4. additionwater (2 L) was added
  5. filtrationCrude 21 was filtered
  6. customdried
  7. customrecrystallised from a mixture of ethyl acetate:hexane (1:6)

出典と根拠

ORDレコード
ord-870c51f8df9d4d22876604cf77809c32
出典データセット
uspto-grants-2010_08
特許番号
US07772352B2

関連ノート

読み込み中…