Diethylene Glycol → 1-Bromo-4-pentylbenzene

HRID 1788618Notes

Reaction equation

HRID 1788618 reaction equation
[C:1]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)(=O)[CH2:2][CH2:3][CH2:4][CH3:5].C(O)COCCO.[OH-].[K+]>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([Br:13])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 817174'-Bromovalerophenone

Product 1

HCID 27355991-Bromo-4-pentylbenzeneYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

95 g (0.39 mol) of 4-pentanoylbromobenzene, 300 ml of diethyleneglycol, 40 ml (0.80 mol) of 100% hydradine hydrate and 45 g (0.80 mol) of potassium hydroxide were heated at 130° C. for 1 hour and then at 180° C. with stirring for 3 hour. Water was added to the reaction solution and the organic layer was extracted with chloroform. After washing the extracted layer with water, the chloroform was removed by distillation. Then the residue was distilled under reduced pressure to yield 75.4 g of 4-pentylbromobenzene having at b.p. 87° to 90° C./2 mmHg.

Workup

  1. extractionthe organic layer was extracted with chloroform
  2. washAfter washing the extracted layer with water
  3. customthe chloroform was removed by distillation
  4. distillationThen the residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5f3fca7fc7f642fd8856543eb8ea740b
Source dataset
uspto-grants-1987_08
Patent number
US04684220

Reaction notes

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