Diethylene Glycol → 1-Bromo-4-pentylbenzene

HRID 1638279Notes

Reaction equation

HRID 1638279 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-pentylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

95g (0.39mol) of 4-pentanoylbromobenzene, 300ml of diethyleneglycol, 40ml (0.80mol) of 100% hydradine hydrate and 45g (0.80mol) 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 75.4g of 4-pentylbromobenzene having at b.p. 87° to 90° C./2mmHg.

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-19576170aabd4738bb756770d024aa48
Source dataset
uspto-grants-1989_11
Patent number
US04879060

Reaction notes

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