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

HRID 1638276Notes

Reaction equation

HRID 1638276 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

50.0g (0.290mol) of p-bromophenyl was dissolved in 300ml of ethanol and 14.2g (0.340mol) of sodium hydroxide and 49.5g (0.300mol) 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 150ml of water was added and the organic layer was extracted with 200ml of hexane. The hexane was removed by distillation thereafter. The residue was distilled under reduced pressure to yield 63.4g of 4-hexyloxybromobenzene having a b.p. 139° C./7mmHg.

Workup

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

Sources & evidence

ORD record
ord-beb0a7fec4da41659977be85fd308bd8
Source dataset
uspto-grants-1989_11
Patent number
US04879060

Reaction notes

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