4-Nitrophenethyl alcohol → 1-[2-[(6-Bromohexyl)oxy]ethyl]-4-nitrobenzene

HRID 2166152Notes

Reaction equation

HRID 2166152 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.[OH-].[Na+]>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 74944-Nitrophenethyl alcoholHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 135927841-[2-[(6-Bromohexyl)oxy]ethyl]-4-nitrobenzeneYield 1,851.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Nitrobenzeneethanol (10.25 g), 1,6-dibromohexane (27 ml) tetra-n-butylammonium bisulphate (1.7 g) and 12.5M aqueous sodium hydroxide (55 ml) were stirred together for 40 h. The mixture was diluted with water (250 ml), extracted with ER (3×350 ml) and the combined extracts were washed consecutively with water (250 ml) and brine (250 ml), dried and evaporated to give an oil (42.6 g). The oil was purified by FCC eluting with ER-CX (0:100→1:19) to give the title compound as a yellow oil (9.52 g). T.l.c. (ER-CX 1:19) Rf 0.11. The following compounds were similarly prepared:

Workup

  1. extractionextracted with ER (3×350 ml)
  2. washthe combined extracts were washed consecutively with water (250 ml) and brine (250 ml)
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-516dee78724c40dbb49cbca4a092ea52
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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