Hydrogen Bromide → 1-(3-Bromopropyl)-4-methylbenzene

HRID 704401Notes

Reaction equation

HRID 704401 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10]O)=[CH:4][CH:3]=1.[BrH:12]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][Br:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 2218933-(4-Methylphenyl)propan-1-ol

Product 1

HCID 140848591-(3-Bromopropyl)-4-methylbenzene

Procedure

3-(4-Methylphenyl)propanol (2.13 g) was heated in 7 ml of 47% aqueous hydrobromic acid under reflux for 5 hours. The solvent was then distilled off under reduced pressure and, after addition of water, the residue was extracted with ether. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was distilled under reduced pressure to give 1.75 g of 3-(4-methylphenyl)propyl bromide. Boiling point: 65° C./0.7 mmHg.

Workup

  1. temperatureunder reflux for 5 hours
  2. distillationThe solvent was then distilled off under reduced pressure
  3. additionafter addition of water
  4. extractionthe residue was extracted with ether
  5. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-fd1850b06e4b44c79be4d76efcef089e
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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