Potassium Hydroxide → 1-Bromo-4-pentylbenzene

HRID 327363Notes

Reaction equation

HRID 327363 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].O.NN.[OH-].[K+]>C(O)COCCO>[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 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 817174'-Bromovalerophenone

Product 1

HCID 27355991-Bromo-4-pentylbenzeneYield 80%

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2A (77.1 g), hydrazine hydrate (46.4 g) and KOH (590 g) in diethylene glycol (250 ml) is heated at 130° C. for 2 h, the excess of hydrazine hydrate is distilled off and the temperature is raised to 200° C. for 2 h. The cooled mixture is poured into 18% HCl, the product is extracted into ether twice and the combined ethereal extracts are washed with water and dried (MgSO4). The solvent is removed in vacuo and the residue is distilled (bp 145°-148° C. at 20 mm Hg) to yield a colourless liquid (58.1 g, 80%).

Workup

  1. distillationthe excess of hydrazine hydrate is distilled off
  2. temperaturethe temperature is raised to 200° C. for 2 h
  3. additionThe cooled mixture is poured into 18% HCl
  4. extractionthe product is extracted into ether twice
  5. washthe combined ethereal extracts are washed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent is removed in vacuo
  8. distillationthe residue is distilled (bp 145°-148° C. at 20 mm Hg)

Sources & evidence

ORD record
ord-33dbd74c3efc4f61a0001fd31322e87d
Source dataset
uspto-grants-1993_12
Patent number
US05273680

Reaction notes

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