Water → 7-Phenoxyheptyl bromide

HRID 610685Notes

Reaction equation

HRID 610685 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[OH-].[Na+].O>CCO>[O:7]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][Br:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 14798Sodium HydroxideHCID 783091,7-Dibromoheptane

Product 1

HCID 105162527-Phenoxyheptyl bromideYield 30.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenol (3.10 g, 33 mmol), 1,7-dibromoheptane (7.74 g, 30 mmol) and NaOH (1.34 g, 33 mmol) were refluxed in EtOH (40 mL) for 30 h. After cooling to room temperature, water (150 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL). The organic phase was washed with water (50 mL) and brine (50 mL), and the mixture was dried over Na2SO4. After evaporation of solvent, the residue was purified by Kugelrohr distillation to give 7-phenoxyheptyl bromide (2.46 g, 30%), bp 126-130° C./0.10 torr, 1H-NMR: 1.2-1.9 (m, 10H), 3.36 (t, 2H), 3.91 (t, 2H), 6.7-7.2 (m, 5H).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×50 mL)
  2. washThe organic phase was washed with water (50 mL) and brine (50 mL)
  3. dry with materialthe mixture was dried over Na2SO4
  4. customAfter evaporation of solvent
  5. distillationthe residue was purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-1ac153f49e8c4b1cad22698d18cdd40f
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

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