1,5-Dibromopentane → 1-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene

HRID 5219

반응식

HRID 5219 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

참가 물질

6

반응물 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 794063-(4-Methoxyphenyl)-1-propanol

생성물 1

HCID 197980251-[3-[(5-Bromopentyl)oxy]propyl]-4-methoxybenzene수율 244.6%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

실험 절차

4-Methoxybenzenepropanol (7.5 g) and 1,5 dibromopentane (30.5 g) were stirred rapidly at RT with tetra-n-butylammonium bisulphate (1.02 g) and 12.5 M aqueous NaOH (36 ml) for 16 h. The mixture was diluted with H2O (170 ml), extracted with ER (3×20 ml) and the combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml), dried and evaporated to give an oil (34.8 g). The oil was purified by [FCS] eluting with ER-CX (0:100→4:96) to give the title compound as a colourless oil (8.83 g). T.l.c. (CX-ER 79:1) Rf 0.1.

후처리

  1. extractionextracted with ER (3×20 ml)
  2. washthe combined organic extracts were washed consecutively with H2O (170 ml) and BR (170 ml)
  3. customdried
  4. customevaporated

출처 및 근거

ORD 기록
ord-b8644227ad934494a702894e391ecfb3
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243076

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