Water → Benzene, 1-bromo-4-(hexyloxy)-

HRID 2120037Notes

Reaction equation

HRID 2120037 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:11](Br)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].O>C(O)C>[CH2:11]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 81011-BromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 520492Benzene, 1-bromo-4-(hexyloxy)-Yield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 200 g of ethanol were dissolved 86.5 g (0.5 mol) of 4-bromophenol and 22 g (0.55 mol) of sodium hydroxide. To the solution at 70° C., 90.8 g (0.55 mol) of n-hexyl bromide was added dropwise. The solution was allowed to ripen for 4 hours and cooled to room temperature, after which 120 g of water was added. The oily matter was separated therefrom and concentrated by a rotary evaporator, followed by vacuum distillation (boiling point 125-128° C./0.5 Torr), yielding 100 g of 4-n-hexyloxyphenyl bromide.

Workup

  1. customThe oily matter was separated
  2. concentrationconcentrated by a rotary evaporator
  3. distillationfollowed by vacuum distillation (boiling point 125-128° C./0.5 Torr)

Sources & evidence

ORD record
ord-32be2b960c52435db374efd12292e7e6
Source dataset
uspto-grants-2004_02
Patent number
US06689530B2

Reaction notes

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