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

HRID 1098712

반응식

HRID 1098712 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3c1511b5ed9349939187fd7999518600
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143325B2

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