Hydrochloric Acid → 1-Bromo-4-pentylbenzene

HRID 1901399Notes

Reaction equation

HRID 1901399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.O.NN.Cl>C(O)COCCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 817174'-Bromovalerophenone

Product 1

HCID 27355991-Bromo-4-pentylbenzene

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of compound 15 (24.87 g, 0.103 mol), hydrazine hydrate (15.45 g, 55% hydrazine content), and diethylene glycol (200 ml), was heated at 130° to 160° C. for 1 hour and water and the excess of hydrazine hydrate were distilled off. The solution was cooled to below 60° C. and potassium hydroxide pellets (17.37 g, 0.309 mol) were added and the solution heated at 200° C. for 2 hours (glc analysis revealed a complete reaction) cooled, and poured into crushed ice (200 g) and hydrochloric acid (200 ml, 6M). The product was extracted into ether (2×200 ml) and dried (MgSO4). The solvent was removed in vacuo and the residue was distilled to give a colourless liquid.

Workup

  1. temperaturewas heated at 130° to 160° C. for 1 hour
  2. distillationwater and the excess of hydrazine hydrate were distilled off
  3. temperatureThe solution was cooled to below 60° C.
  4. additionpotassium hydroxide pellets (17.37 g, 0.309 mol) were added
  5. customa complete reaction)
  6. temperaturecooled
  7. additionpoured
  8. extractionThe product was extracted into ether (2×200 ml)
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed in vacuo
  11. distillationthe residue was distilled
  12. customto give a colourless liquid

Sources & evidence

ORD record
ord-15ea0a9856e943a2bcbb815f465b10ac
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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