1-Bromohexane → 4-Hexyloxy-3-methoxybenzonitrile

HRID 1595312노트

반응식

HRID 1595312 반응식
[H-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CN(C=O)C>[CH2:15]([O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:12][CH3:13])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

참가 물질

5

반응물 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 781354-Hydroxy-3-methoxybenzonitrile

생성물 1

HCID 217050324-Hexyloxy-3-methoxybenzonitrile수율 35.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매4회

실험 절차

To a suspension of sodium hydride, 60% dispersion in oil,(4.8 g; 0.11 mol) in 40 mL of DMF, a solution of 4-hydroxy-3-methoxy-benzonitrile (14.9 g; 0.1 mol) in DMF (40 mL) was added dropwise over 10 minutes. After addition, the reaction mixture was stirred at ambient temperature for 30 minutes, then bromohexane (16.5 g; 0.1 mol) in DMF (20 mL) was added. The reaction mixture was stirred at ambient temperature for 18 hours. The DMF containing reaction mixture was concentrated to a residue, and H2O (100 mL) was added to the residue. The solid was collected by filtration to obtain 8.2 g (35% yield) of the tide compound as white solid. 1H-NMR (DMSO-d6; 200 MHz) δ7.45 (s, 1H), 7.42 (s, 1H), 7.1 (d, 1H), 4.0 (t, 2H), 3.8 (s, 3H), 1.6-1.8 (m, 2H), 1.2-1.5 (m, 8H), and 0.9 ppm (t, 3H).

후처리

  1. additionAfter addition
  2. stirringThe reaction mixture was stirred at ambient temperature for 18 hours
  3. concentrationwas concentrated to a residue, and H2O (100 mL)
  4. additionwas added to the residue
  5. filtrationThe solid was collected by filtration

출처 및 근거

ORD 기록
ord-43b569c685f44287a2cbdfbfa30f03a2
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288100B1

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