Hydrogen Bromide → 4-(3-Bromopropyl)phenol

HRID 2417990Notes

Reaction equation

HRID 2417990 reaction equation
[BrH:1].O[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1>O>[Br:1][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 824523-(4-Hydroxyphenyl)propanol

Product 1

HCID 148170364-(3-Bromopropyl)phenolYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 48% hydrobromic acid solution (110 g) was added 4-(3-hydroxypropyl)phenol (25 g) and heated on a steam bath for 3 hours. After cooling, water (500 ml) was added, the oil was extracted with ether, washed with water and then with dilute sodium bicarbonate solution. The etheral extract was dried over potassium carbonate, evaporated and the residue was distilled in a Kugelrohr apparatus giving 29.6 g (84%) of 4-(3-bromopropyl)phenol, bp 180° (2 mm). The product was 92.6% pure by gas chromatography and mass spectrum was compatible with 4-(3-bromopropyl)phenol.

Workup

  1. temperatureheated on a steam bath for 3 hours
  2. temperatureAfter cooling
  3. extractionthe oil was extracted with ether
  4. washwashed with water
  5. extractionThe etheral extract
  6. dry with materialwas dried over potassium carbonate
  7. customevaporated
  8. distillationthe residue was distilled in a Kugelrohr apparatus

Sources & evidence

ORD record
ord-7a4a9b68a7b04eec8c287a132d269c07
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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