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

HRID 1788615Notes

Reaction equation

HRID 1788615 reaction equation
[OH-:1].[Na+].[Br:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C(O)C>[CH2:4]([O:1][C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][CH:6]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 81011-BromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 520492Benzene, 1-bromo-4-(hexyloxy)-Yield 164.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

50.0 g (0.290 mol) of p-bromophenyl was dissolved in 300 ml of ethanol and 14.2 g (0.340 mol) of sodium hydroxide and 49.5 g (0.300 mol) of 1-bromohexane were added thereto. The resulting solution was stirred at 70° C. for 4 hours to complete the reaction and the solvent was removed by distillation. Then 150 ml of water was added and the organic layer was extracted with 200 ml of hexane. The hexane was removed by distillation thereafter. The residue was distilled under reduced pressure to yield 63.4 g of 4-hexyloxybromobenzene having a b.p. 139° C./7 mmHg.

Workup

  1. customthe reaction
  2. customthe solvent was removed by distillation
  3. additionThen 150 ml of water was added
  4. extractionthe organic layer was extracted with 200 ml of hexane
  5. customThe hexane was removed by distillation
  6. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-e10bdcdc08734a1eb2de660877144002
Source dataset
uspto-grants-1987_08
Patent number
US04684220

Reaction notes

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